Caitlin and James Part three
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Caitlin And James - Part Two free porn video
Caitlin and James - Part two
By Cherie Peterson
Chapter five
"Oh Caitlin, he's getting so excited about going on a date with you."
"He begged me to go shopping with him for a special outfit for your
night together. He even wanted to get some nail polish, special
lingerie, a nightie and a negligee. I think he's expecting to get
lucky," Justine says with a wink.
Justine and I are on the train and she is telling me about the
preparations James is making for our first "official" date.
I asked the sweet adorable feminine boy on a date a couple of days ago
but I won't be able to take him to dinner until tomorrow night.
"Did you tell him your favorite colour is turquoise?" Justine asks.
I tell her that it, along with aqua-like blues are my favorite colours
but I don't remember telling him that.
I'm suddenly getting very excited about tomorrow night, hoping he'll
wear a dress.
"Well everything he's bought for the date is turquoise, even the
earrings."
"What type of earrings?" I ask.
"Button earrings of course, they're his favorite type of earrings, he
likes being little Miss Prim and Proper. Well, we call him that,"
Justine says.
"What type of outfit? Is it a dress?" I ask a little hopefully. I love
the thought of my boy toy James wearing a dress to look pretty for me
for our big date.
"He's really not that into wearing dresses, he likes androgynous
feminine outfits, and most of all wearing earrings and his hair in
feminine hairdos.
"It's a black and turquoise waistcoat outfit, black ladies pants that
zip up on the left side, a black and turquoise waistcoat and a turquoise
blouse," Justine explains.
I try to look enthusiastic but I was really hoping he'd wear a dress.
'What's up Caitlin?"
I tell her and Justine tells me that James wore dresses quite a bit in
his teens but doesn't do that anymore.
"I'm sure if you ask nicely he'd be happy to wear a dress for you, he's
so infatuated with you," she said.
"Get this. He's made an appointment to get a perm tomorrow afternoon,
especially for you. What guy would do that for a woman?" Justine says
reaching over to put a hand on my shoulder."
I ask Justine who dressed him up as a teenager, his mum, sister or a
girlfriend?
No, he didn't have a sister and his mum had short hair and hardly wore
any jewelry and makeup," Justine says.
"You should ask him about his Aunt Mary, she is very special to him. She
taught him everything about being a girl, well, a girly boy. When she
died a couple of years back she left everything to him. Her house, her
money, her jewelry, clothes, everything.
"That gold broach he wears quite often was her favorite piece of
jewelry.
"Her dying wish was that he wear it regularly in memory of his aunt, a
promise he's been more than happy to honour nearly everyday," Justine
explains.
"If he loves you half as much as his aunt you'll be the happiest person
in the world."
I suddenly realise it's time for me to get off the train. I say good bye
to Justine and tell her I can't wait to see James again.
Chapter six
When I wake up the following morning I go to the window and look
outside.
It's blowing a gale, I start thinking about James' perm, I feel a bit
sad for him going to all that trouble and expense to impress me only to
have a bit of wind ruin it for him.
__________________________________________________
At the end of the day I start getting ready for our date, touching up my
subtle makeup and brushing my hair.
I look outside and see that it is still very windy, I decide to put my
hair in a ponytail.
I get in my car and head over to James' building to pick him up.
On the way over I fantasize about what he'll be wearing.
I go into the switchboard room where he works and he's not there.
"Oh hi Caitlin, he's in the ladies, touching up his makeup, making
everything perfect for you," James' friend Siobhan says.
"Is he allowed to use the ladies toilets?" I ask.
Sorry, just kidding. No, he uses the unisex toilet. he's still allowed
to use the men's loo but he gets nervous about doing his makeup in the
men's," Siobhan replies.
Siobhan turns her eyes away from me and looks at the doorway. I turn
around and see James.
Well, first of all, there is no perm. He has his hair in a plaited bun
on top of his head. Justine's description of his outfit yesterday was
perfect, but she forgot to mention he would be wearing a silver and
turquoise broach at his top button.
The hair looks adorable, only something you'd see in a movie.
His outfit is not all turquoise but mainly black with touches of
turquoise - very tasteful.
I go up to him and greet him with a kiss, telling him he looks lovely
and that I love that colour.
"I know, you told me it is your favorite," James says.
He tells me my outfit looks fantastic, which I find a little strange,
it's not as elaborate as his. I'm wearing a navy blue pants suit, with a
white blouse and in my pumps I'm noticeably taller than James.
We depart with him clutching my right arm with both of his hands.
In the lift alone together, I can't resist, I grab him and kiss him
until the lift gets to the ground floor.
Such a, beautiful, unique, charming boy!
We hold hands as we walk to my car. I tease him a little by telling him
that Justine said he was going to get his hair permed especially for our
date.
"So you suddenly don't think I'm worth that type of trouble," I ask, in
a bit of a mock protest.
Poor James doesn't seem to get the joke.
"I'm sorry Caitlin, I really wanted my hair to look pretty for you but
it's so windy outside it would look messy, I decided to play it safe but
with something a little bit different," he says.
I hold the car door open for him and tell him to get in the car.
"So you got the hairdresser to do that bun for you," I say.
He tells me he did the hairdo himself.
"There's no way you did that hairdo yourself, I bet Justine or Siobhan
did it for you," I close his door and walk around to the driver's side
get in and add:
"Those pigtails you were wearing when I first saw you, I can just
imagine Justine and Siobhan standing either side of you at work doing
them for you."
"I did them myself, my auntie showed me how to plait my hair when I was
young," he protests.
"This hairdo is very easy to do, you just put your hair up in a
ponytail, plait the ponytail and wrap it around to form a bun."
"Well it looks very pretty," I kiss him and drive off.
On the drive over I tease him a bit more by telling him that I'm
disappointed that he's not wearing a dress. The reaction is not what I
imagined it would be. He apologised! James said he hardly wears dresses
anymore and that he didn't know I wanted him to wear a dress.
We get to the restaurant, I take his hand as he gets out of the car, he
then hugs me and kisses my neck.
"Do you like me being feminine? I've always hoped this would happen but
I've never known a woman to like me as a boyfriend because I'm feminine,
I almost gave up on it." he asks.
I tell him it's one of the best things about him, I kiss him on the
forehead, he takes my arm and we walk into the restaurant.
My usual waitress takes us to our table, she sits him down, I order my
usual bottle of wine for both of us.
After looking at our menus for a while James asks if I come here
regularly. I tell him yes and suggest a couple of items that he might
like, he tells me he likes them and what he'll have.
Lisa brings over the wine, she pours for him first.
I order for both of us, James asks for a glass of water.
"Of course sweetie," Lisa says touching him on the shoulder.
She compliments him on his earrings and asks him where he got them.
James is silent, blushing with embarrassment, but Lisa waits for an
answer.
"Sportsgirl," he mumbles.
"Oh, that's my favorite shop too."
I love the thought of my guy shopping for earrings for himself, or
anything really, at Sportsgirl.
Lisa notes that button earrings seem to be coming back into fashion,
she's noticed several other young women wearing them.
"Nice to see a boy with such great taste wearing them as well," she adds
touching his shoulder again.
James turns away from her and blushes furiously. He probably thinks Lisa
is making fun of him.
As Lisa departs, I reach over and take his hand, he seems incredibly
nervous. Probably my teasing on the way over didn't help.
I ask him about his Aunt Mary.
His eyes immediately light up and he talks almost non-stop throughout
the whole meal about her, saying on more than a couple occasions that
she is the "most wonderful person ever".
"She was a super-model before there were super-models, after that she
owned a chain of clothing stores with a few friends."
Basically, it was her who introduced him to all things feminine, taught
him about clothes design, cooking, make up, feminine hairstyles. James
said it started soon after he started going over to Mary's place every
afternoon after school, when he was nine years-old, to keep her company
after his Uncle Keith died.
"She didn't take his death at all well. Over the school holidays I lived
there until mum thought auntie was okay but from then on we became very
best friends," James said.
He mentioned that all the girly stuff started when his aunt caught him
trying on her dresses and clip-on earrings. The third time it happened
they sat down and had a good talk about it and agreed that they would
have secret dress up sessions and she made sure he always had a
collection of his own dresses, skirts and heels, make up and jewellry.
"I think Auntie Mary enjoyed the dressing up a little bit more than I
did," James said.
Soon after that, Aunt Mary took charge of his grooming and bought all
his clothes. She also started taking him to her hairdresser and
beautician, he has never had short hair since.
"Mum said Aunt Mary's taste in clothing for me was 'twee', but if I
truly liked the clothes then it should not be a problem."
However, his two elder brother's gave him a hard time and his father was
a bit standoffish. To combat this Aunt Mary told him he should use his
"girly" skills to be "mummies' little helper" - so he started helping
his mum with the housework and the cooking to the point that his mum
started going back to work part-time. He said the best thing about that
was in some aspects of the household he had authority over his two elder
brothers, something that his dad and mum always backed his up about.
"Dad was very happy mum was back working and acknowledged my role in
that when he said: "Your mum loves being back at work and we really
appreciate your help."
There were two shocks to the family though.
During the Christmas school holidays when he was 12, without any notice
to the family and to James' absolute delight, Aunt Mary decided to get
James' ears pierced and get him his first few sets of earrings. Many
guys at the time had one ear pierced but two was very rare.
"As well as a pair of gold studs, we got a few pairs of small hoops and
on Christmas Day Aunt Mary gave me a pair of diamond studs, James said.
"Nowadays lots of guys wear diamond studs in both ears but I was the
first one.
"We also got a pair of big gold hoop earrings, the ones you saw me wear
when we first met, which Aunt Mary called my 'secret earrings." The
family didn't know about them until my 16th birthday."
His aunt arranged for a sweet sixteen birthday party at her place and
convinced James to finally wear a dress in front of the family, there
were also a few (girl) schoolfriends there, who already knew of his
dressing up.
He did wear a dress, heels, lipstick, make-up, had his hair permed and
wore the big hoops, but none of the family seemed shocked. He even got a
few compliments. He found out later his aunt warned everyone beforehand
and encouraged them to be sympathetic.
Throughout this one sided conversation James' mood has completely
changed. When we first came in he could hardly look or speak to our
waitress Lisa but when she cleared away the main course plates he gushed
at her and said the meal was "adorable".
Lisa promised she would pass on the compliment. When she came back to
get our coffee orders, James said he needed to go to the "bathroom".
Yes, he said bathroom, not toilet or the loo - very polite.
Lisa seemed hesitant, a thought then popped into her head and she
grabbed his hand and told James to come with her.
When Lisa came back with our coffees, she told me she led him to some
single stall toilets, that the staff use.
"I didn't think it would be safe for him to be dressed like that,
touching up his make up in the men's loo and I think some women would
object to him using the ladies," Lisa said.
I thank her for her kindness and she told me if he's ever nearby and
needs the loo he's welcome here anytime.
James comes back to the table and sits down and Lisa, who has been my
waitress at this restaurant for about a year, asks how we know each
other.
"Oh, he was my knight in plaited pigtails when we got stuck in a lift
last week. The least I could do is take him out on a date," I say to
Lisa.
"You two are dating? NO WAY," she says in shock. "You're very lucky,
he's so cute."
As I'm signing the credit card slip. Lisa asks James who did his hair.
James tells her and even undoes his bun to reveal a plaited ponytail and
shows Lisa how it's done.
I notice a few women at adjoining tables pointing and smiling. Funny, I
usually get all the attention he's getting.
He puts his hair back in a bun then Lisa leaves and says goodnight.
"Well, it looks like you've made a new friend and a few admirers," I say
to James.
James looks at me.
"I lean over to him and whisper, "Lisa and those two ladies."
I point to them and they wave back.
A few moments later we're walking out the door and I take James' hand.
"You two are a very lovely couple."
The two older ladies are behind us, the one with the long dark hair
compliments James on his clever hairdo and asks if James is a
hairdresser.
The other one with short curly hair says I should be careful.
"That waitress was shamelessly flirting with your boy."
We walk off to the cinema and see our movie. For most of the movie
James' head rests on my shoulder and I have my arm around him.
Chapter Seven
We talk about the movie on the drive home.
I pull up at his place and park in his driveway.
We kiss and fondle each other for a bit.
I'm not hearing any invitations, so I take the initiative and ask to use
his bathroom.
After I come out of his bathroom, I notice a bottle of wine on the
kitchen counter, two wine glasses, a bottle opener and a small silver
tray of chocolates.
I have a little giggle - I'm not the only one having naughty thoughts.
As I'm opening the wine, I hear some footsteps. I call out to him that
these are delicious chocolates and ask him where he got them.
"I made them myself." he says.
"What?" I turn around to talk to him but I'm so stunned I can hardly
speak.
James is wearing his straight, luscious brunette hair down and is
wearing the most beautiful nightie - turquoise of course, in keeping
with the theme of the evening.
I'm still speechless, he is the personification of feminine beauty.
"I'm sorry again for not wearing a dress Caitlin. I hope this partly
makes up for it," James says, a little bit shyly as he plays with the
ends of his hair that fall just past his shoulders.
I rush up to hug him we kiss and snuggle some more.
"Sweetheart, you look so beautiful, I'm never going force you to wear
anything you don't want to," I say pressing his face into my breasts.
As we hug and as I grab his firm ripe butt I realise he's not wearing
anything under his nightie.
We separate and go to sit on the couch and drink the wine.
I pop two of his chocolates into his mouth and start French kissing him
and use my tongue to collect one of those chocolates for myself.
We separate and he starts giggling and starts unbuttoning my blouse.
Once the blouse is off he starts hugging me and reaches around to undo
my bra but I brush him away and we stand up.
He then reaches around to undo the button and the zipper on the back of
my pants, which I let him do.
My pants drop to the floor, I step out of my heels.
We separate and look at each other for a couple of seconds, he in his
nightie, me in my stockings, panties and bra.
We hug again and when we do I realise he has an enormous erection.
After he kneels down to take off my stockings we head for the bedroom.
Chapter eight
I wake up to a humming sound, after a couple of minutes it stops.
I try to orientate myself and realise I'm in James' bed, he's not here
though.
I notice my suit is on a hanger hanging on the door. I think I left them
in the lounge room last night.
I remember taking off my bra in bed but not my panties and now I can't
find either.
I see him walk past the doorway, a couple of minutes later he walks in
with a mug of coffee for me.
He's still wearing his nightie and he is wearing a negligee that matches
the nightie.
What is really surprising is he's got rollers in his hair.
He gives me my coffee and kisses me good morning.
I make sure my breasts are covered.
I ask him how he knows how I like my coffee.
"You had coffee in the restaurant last night, I took a mental note of
how you took it," he said turning to the wardrobe, he takes out a
dressing gown and puts in on the bed for me.
"Do you like eggs benedict?" he asks.
I nod. I can't keep my eye off his rollers.
"Well how about I make some for you and you can have breakfast in bed,
unless you want something else."
"No that's fine," I say.
He then kisses me on the forehead and tells me he won't be long.
While he's gone I try to remember last night.
When we entered the bedroom last night, James suddenly became nervous so
we just cuddled each other in bed then eventually went to sleep.
Now I remember! In the middle of the night he woke up and gave me oral
sex, I initially was half asleep when he started on me and I fell back
to sleep soon after I climaxed.
Back to the present, and smells waft in from the kitchen.
Several minutes later James walks into the bedroom.
The rollers are out of his hair, which is now a sea of pretty curls.
He's also wearing large silver hoop earrings and bright red lipstick.
I love the contrast of the pretty curls and the straight bangs.
The tray has legs which allows me to sit up and have breakfast in bed. I
carefully make sure my breasts are still covered, he's not going to get
a look that quickly, I'm a little shocked with what he did to me last
night.
He moves to the other side of the bed and sits cross legged on the bed
facing me, I'm sure hopeful for a look at my breasts, I'm getting a
little disappointed that he's just like any other bloke who can't wait
to get a look at my breasts. Well James like every other guy has to earn
that right.
I realise this whole time I've been staring at him with my mouth agape.
James take a small plate of food and a napkin off my tray.
He pats his hair in a very girly way, smiles and asks me what I think.
"You look lovely sweetheart, is this a home perm."
"No I just washed it, put rollers in it and spent a few minutes under
the hair dryer."
Under the hairdryer? I think to myself.
"Caitie, aren't you going to eat?"
I turn my eyes to the tray and there's a big plate of eggs benedict,
cutlery wrapped in a cloth napkin two glasses of orange juice, and a
small vase with a single red rose.
I take the rose and smell it and reach over to put it in his hair just
above his ear. James smiles and bats his eyelids.
I then start on the eggs.
A few minutes later, James leaves the bedroom and comes in with a white
t-shirt and a couple of plastic packets and puts them on the bed.
"Please don't be angry at me Caitlin."
Angry? "What's the matter sweetheart."
"I started to wash your underwear and your blouse so you have something
clean to wear this morning but then I noticed the label on your blouse
says don't machine dry and you can't machine dry bras either. I'm
sorry," James say a little nervously.
"It'll take a while for them to dry.
"I've got some panties here that might fit you that I've never worn and
here's a t-shirt that may fit, I'm sorry again I didn't mean to leave
you naked."
I look at him in his curly hair, a red rose in his hair, eye shadow,
mascara, bright red lipstick, big silver hoop earrings and matching
bangles, a nightie and negligee in a colour chosen because it's my
favorite colour.
It doesn't escape my attention that he's done all of this to please me.
I hold out my arms and motion to him to come to me. He leans over and we
hug.
I whisper into his ear that I can't be mad at anyone as pretty as him.
I kiss him several times on the neck and he kisses me on the cheek.
"Could you do me a little favour darling."
"Of course."
"In the boot of my car is a brown leather bag, could you get it for me?"
I say.
He kisses me again and leaves.
While he's gone I finish breakfast, it's delicious.
A few minutes later he comes back and starts laying out my change of
clothes on a chair in the bedroom.
"I think Caitie was having naughty thoughts yesterday," James says
laying out my jeans.
I look at him and think about how pretty he is and how attentive he's
been to me.
Guys would be jealous of me, not him!
"These are lovely boots," as James says that I notice he's getting an
erection.
"Sweetheart could you take my tray."
While he's gone I grab a mirror on his bedside table and notice lipstick
marks on my cheek, I wipe them off with a tissue and fix my hair a
little.
He's been such a good sissy, he should be rewarded.
My very beautiful boy comes back to the bedroom and I tell him to take
off his gown. He smiles at me and lets it slip off.
"And the nightie." I say.
James hesitates, I respond by throwing back the bed covers to reveal my
naked body.
I smile cheekily at him.
He takes off his nightie to reveal a huge erection.
James leaps on the bed and his hair and his earrings bounce about.
He starts kissing my breasts.
"Steady on princess, just lay back and let Caitie do all the work," I
say turning him on his back.
He reaches for his bedside table and I notice one of his earrings is at
an awkward angle, twisting his earlobe too much, I adjust it and lean
forward and feel his erection rub against me down there.
He keeps reaching over to the bedside table, I open the top drawer and
see a box of condoms, I take one and unwrap it. I then start to kiss his
neck and as I do James kisses me.
I move to kiss his hairless chest and then his hairless stomach and then
his abdomen, then I start kissing the shaft of his penis.
I put the condom in my mouth and put it on his penis only using my
mouth.
I then move my crotch over his penis and let the strong shaft rub
against me.
As I do so, I look at his made up pretty face, he is making kissing
motions with his luscious red lips. He bats his eyelids showing off his
eye shadow. I think for a few seconds about all the preparation he has
done just to impress me, getting up early to put his hair in rollers, I
imagine him doing his hair and doing his makeup while my breakfast was
cooking. I imagine him shopping for sexy nightwear to wear just for me.
I'm so lucky to have this precious, lovely little lady boy as my own!!
I lean forward, to kiss him and kiss him and kiss him. As I do he
reaches for my breasts and starts rubbing them. I lean back and grab his
hands interlocking our fingers.
I take one last look at him, noticing how his pretty silver earrings
contrast against his curly black hair and glitter in the morning
sunlight coming though the cracks of the curtains.
I close my eyes as I lower my body on to him and let him inside me.
Our breaths get deeper and louder, we start to breath in synchronicity.
He starts moaning, I start moaning. He whispers, "Oh Caite, oh Caite".
He climaxes the moment I do, yelling: "I love you Caitie!"
I lean forward to kiss his beautiful lips, moving him out of me.
We then lay on the bed with me in his arms, my head resting on his
shoulder.
He pulls the bed covers over us and we lay in bed and enjoy the warm
afterglow.
(To be continued)
Lesley
- 21.11.2020
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