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"Kyle, you haven't forgotten that we're invited for dinner at the
Watsons tonight?" asked Simone, Kyle's wife.
"No, I hadn't forgotten," Kyle replied. "I'll try to get out of the
office early, so that I have plenty of time to get home, have a shower
and get ready."
"Do you remember what happened when the Watsons came here for dinner two
weeks ago?"
"Remember? How could I forget? That was when Hannah Watson, her tongue
loosened by several glasses of Sauvignon Blanc, told us that Jack Watson
liked to dress in women's clothes and call himself Katie."
"Exactly," Simone said. "And if my memory serves me well, Jack (or
should I say Katie?) promised that tonight he (or should I say she) will
be wearing a frock."
"Yes, your memory is correct. I must confess that a few times in the
last two weeks I've found myself wondering what he will wear and what he
will look like," said Kyle. "Will he wear a frock or will he bottle it?
What will he be wearing with the frock? Will he be wearing heels? Frilly
undies? Stockings? High heels? Make-up? A wig? Perfume? Will the frock
be short or long?"
Simone replied, "I've been curious too. I Googled crossdresser and then
clicked on images. Some of the crossdressers were very feminine. They
looked like women. Some were wearing women's underwear. They were all
wearing make-up. It seemed that they shave their legs. They were wearing
sexy but uncomfortable footwear. Most of the dresses and skirts that
they wore showed off their legs."
Simone could practically see the thought process in Kyle's brain.
Women's underwear. Make up. Shaven legs. High heels. Short dresses.
"I don't suppose Jack is any different," Simone said. "Anyway we'll find
out today. We're due that at seven for seven thirty."
Kyle replied, "I can hardly wait. Shall we get there at seven? I'm very
curious."
"Well you'll have to hold you curiosity in check. I don't think we can
arrive at seven, darling. It will take a long time for Jack to make
himself look pretty. If we arrive too early he may not be ready."
Kyle nodded in agreement. "I suppose so," he said in a voice that
sounded a little disappointed. He smiled to himself about the idea of
Jack shaving his legs and the thought of Jack wearing lipstick and
eyeliner.
"And I don't want any sexist or rude comments, Kyle. If Jack wants to
wear a dress, that's entirely up to him. It's a free country and we
should celebrate our diversity."
"Sure. What are you going to wear?" asked Kyle. It was easy for men.
Smart casual. Smart trousers, a new shirt and shiny shoes. It was harder
for women and t-girls; skirt or dress? long or short? plain tights or
black?
"Oh I don't know," said Simone. "I haven't decided yet," she lied.
Hannah Watson always scrubbed up well. She always looked a million
dollars. Simone never liked being overshadowed by Hannah so she'd bought
a new black and white patterned dress last week. It was lovely, a little
short maybe, it must have been mid-thigh but she liked being a little
risqu? sometimes. She hadn't even shown Kyle the dress yet. That could
wait till this evening.
She'd wear the new dress with plain tights and black strappy sandals, a
bracelet and a thin necklace. But what would Jack be wearing?
***
"Jack, you haven't forgotten that the Watsons are invited for dinner
tonight?" asked Hannah, Jack's wife.
"No, I hadn't forgotten," Jack replied. "I'll try to get out of the
office early, so that I have plenty of time to get home, have a shower
and get ready."
"Do you remember what happened when we went there for dinner two weeks
ago?"
"Remember? How could I forget? That was when you had too many glasses of
that lovely Sauvignon Blanc and when we were discussing hobbies, you
announced to all and sundry that my hobby is to dress in women's clothes
and call myself Katie."
"Yes, Jack," Hannah said. "And if my memory serves me well, you promised
to wear a frock tonight."
"Yes, your memory is all too correct, Hannah. You got drunk, made your
announcement and then bullied me into agreeing to spend this evening in
drag. I must confess that a few times in the last two weeks I've found
myself wondering if I can wriggle out of it. At other times I've thought
I've got to take it like a man - a man wearing a dress, heels, make-up
and a wig."
"They're due that at seven for seven thirty."
"Seven?" It takes a long time to make myself look pretty. An hour and a
half on a good day. Sometimes two hours. That means I've got to be home
by five thirty but preferably five. I hope they don't arrive early.
Katie won't be ready."
"Don't worry. I told Simone not to be a minute before 7.30. I'm planning
to wear that vintage dress I got last week. You know the one."
Jack nodded. As a crossdresser he took a good deal of interest in
women's clothes including Hannah's dresses. This one was in a pale green
floral print with a tie around the waist. It was both cute and
practical. It was about two inches above the knee - perfect for a
hostess at a dinner party on a warm summer's day.
"More to the point, what are you going to wear?" asked Hannah. "I don't
want you to wear anything that shows off your panties. I think it would
be embarrassing if you wore something slutty."
"Something slutty? All my dresses are slutty, darling," said Jack
smiling. "I haven't decided yet," he lied. Hannah and Simone always
looked smart and beautifully dressed. Jack didn't want to be
overshadowed by either of them.
"I was hoping you'd wear that lovely chiffon dress," Hannah advised. It
was turquoise with black polka dots in a floaty chiffon fabric. Around
the neck were two tiers of the same fabric which made the dress look
cute. It was not too short coming down to about four inches above the
knees. It rustled with every footstep and was fun to wear.
"I was thinking more of my brown and white leopard print bodycon dress,"
said Jack.
"Bodycon? You mean stretchy and skin-tight? It's so tight it shows your
bra straps and panty lines."
"It's so soft and lovely to wear."
"It may be but it shows every bulge underneath - some of which you don't
want visible."
"Oh don't be such a fuddy-duddy," Jack said.
"Oh I agree it's totally sexy and very sophisticated but it may be too
sexy for an occasion like this. It may be midi-length but because it's
tight when you sit down it rides up. Your panties may well be
visible..."
"Oh come on, Hannah. Stop being so negative."
"Ok but you must try it on this evening to show me how it fits. Then we
can make an informed decision."
"OK," said Jack disappointed. But he knew he'd still wear that dress
come what may. Jack (or rather Katie) would wear the skin tight dress
with plain tights. He'd wear stockings if he could get away with it. He
would wear black court shoes. To set off the outfit he'd wear gold ear-
rings and a gold bracelet.
***
Time always drags when you have something to look forward to. Today was
no exception for Kyle, Simone, Hannah and Jack/Katie. Whenever Jack had
a night out as Katie, he found it very difficult to concentrate at work
before hand. He was thinking of possible underwear combinations, which
wig to wear, how to do his makeup, whether he could last all night in
those shoes.
He had once counted how many wigs he owned. The answer was 17;
blonde/brunette, long/bobbed, straight/curly - he had a lot of variety.
He'd also worked out that he owned 27 dresses, even more skirts and 15
pairs of shoes. He had nearly as many handbags. Hannah didn't quite
understand. You can only use one bag at a time.
At last, the time to pack up and leave work arrived. Jack headed home as
quickly as possible to begin the process of becoming Katie. As he would
be under the scrutiny of his friends Kyle and Simone, everything had to
be as near perfect as possible.
Fortunately their house had two bathrooms. Jack did not have to worry
about stopping Hannah from getting ready. As soon as he got home, Jack
made himself a cup of tea and then headed for his bathroom. He had a
quick shower and then put on a dressing gown while he did his face.
First he had to shave as closely as possible. Then it was on with the
underwear - matching pink bra and panties and a pair of natural coloured
tights. He up on the panties and then used a device called a nu-bra to
create a realistic cleavage. He put on the bra, did it up at the back
and slipped two silicon breast forms in the bra cups. He checked the
mirror. It looked great.
Then he had to apply the various cosmetics; skin prep, moisturiser,
beard cover, foundation, powder and blush. Jack never could understand
why this all took so long but he was a perfectionist.
His eyes took even longer. Today he wore false eye-lashes, glued to the
top lid and thickened with mascara. Then there is eye-shadow to apply
and then eye-liner. Yes he thinks he has done a good job. A smear of
lippy and he's nearly done.
Time for the brown and white leopard print dress. Jack went into the
spare room where the dress was laid out ready. He put it on carefully so
as not to smudge the makeup he had just completed. It came down to his
knees, maybe an inch or two longer. He looked in the full length mirror.
Great. Now the black court shoes with the three inch heel.
Now which wig? Brunette he thinks. Blonde can be slutty. Shoulder
length? Yes. There they all were - all 17 on polystyrene heads.
"Darling," Simone called out from the kitchen. "You haven't forgotten
that I wanted to check that dress is OK, have you?"
"No," called Jack. "I'm in the spare room wearing it."
"OK. Give me a minute. The food is nearly all ready."
Jack chose the wig he wanted, brunette, straight and shoulder length. He
put it on. This was the time when he stopped being Jack and started
being Katie; when he looked feminine. He started to brush the wig,
teasing it this way and that.
Hannah came in. She was looking very pretty in the pale green floral
print dress. "Wow. You look gorgeous, my darling," she said. "That
dress looks great but is it decent, Katie? Give me a twizzle."
Katie spun on her heels.
"OK. Sit on the bed."
Katie did as she was told and the dress rode up revealing half Katie's
thighs. But it wasn't indecent. Katie's pink panties were well hidden.
"OK. It will do. I'd prefer the green and black polka dot number but
that dress is fine. They'll be here in five."
"I've still got to finish my hair, add the jewellery and double check
the makeup. Then I'll be done." A burst or two of hairspray would hold
the wig in place.
***
"The taxi's here." Simone called.
"OK," said Kyle. He was comfortably but smartly dressed in a jacket and
jeans. He quickly walked down the stairs.
Simone was waiting wearing the black and white print dress.
"Wow that dress is great, darling."
"Thanks. I hope it's not too short. Now just remember, no talking about
Jack when we're in the taxi. Even the most confidential of secrets can
get revealed by careless talk."
"Mum's the word."
They got in the taxi and were silent for the whole ten minute journey.
Kyle was wondering what Jack (Katie) would look like. A man in a dress
or a babe?
***
Ding dong went the front door bell. Hannah ran to open it. "Simone,
Kyle, great to see you. Come in."
She opened the front door wide. The guests went inside and followed
Hannah to the lounge. "I love that dress, Simone. Is it new?"
"Fairly."
"Sit down, sit down," Hannah said and Kyle and Simone each took a chair.
"Katie's upstairs; she's nearly ready, just the finishing touches - you
know what women are like."
Both Kyle and Simone nodded."
"Oh here she is." Hannah could hear Katie's shoes stomping down the
stairs and across the hall. Katie took a deep breath, opened the lounge
door and went in, hips swaying in a feminine manner.
"Simone, Kyle, hi. What a great dress, Simone. It's a great length."
'How do you greet a crossdresser?' wondered Kyle. Simone jumped up from
her chair. "Thanks, Katie, but wow don't you look fab?" She walked
towards Katie and gave her a girly hug and an air-kiss on each cheek.
"Mwah, mwah."
Kyle jumped up too, till wondering what to do. He hadn't expected Katie
to be so feminine and so attractive. He offered Katie a very male hand
shake. "Drinks everybody?" Hannah asked. "I have Sauvignon Blanc in the
fridge."
"Sure," said Kyle.
"Suits me," said Hannah.
"And me," said Katie.
"I'll help you," offered Simone and she followed the hostess into the
kitchen leaving the two men in the lounge.
Simone shut the kitchen door behind her. "That smells great." Hannah got
a bottle of wine out of the fridge. She had already got the glasses and
corkscrew handy.
"Your husband is a bit of a babe," said Simone. "Well more than a bit of
a babe. A total babe."
Hannah smiled.
"If I saw Katie in the street I would never have recognised her.
Honestly I'd think that she was a woman. An attractive woman at that
with great legs," said Simone.
Hannah smiled again and removed the cork from the bottle with a loud
pop.
If Kyle looked that good in a frock I'd consider dressing him as a girl
every night and calling him Kylie."
Hannah laughed as she poured out the four glasses of wine. "I'd just
watch that husband of yours. You know he chases anything in a skirt."
"Chased, Hannah. Not any more. He has learned to keep his hands to
himself. Anyway I'd be surprised if he was interested in a man."
"Not even a very pretty man like Katie?" Simone asked. "Ready?"
"Yes," said Hannah.
***
"You look fantastic, Katie," said Kyle after the two wives had gone into
the kitchen. "Never in a million years did I think you'd look so good,
so feminine.
"Thank you. Sit down, Kyle," instructed Katie. Kyle sat back down in
the chair he'd chosen earlier. Katie sat down in another chair, opposite
Kyle. Not unexpectedly her dress rose part way up her thighs.
"Honestly what do you think?" Katie asked.
"Christ, Jack, you never told me you were DDG."
"Don't call me Jack. I'm Katie. DDG?"
"Sorry, Katie. DDG means drop-dead gorgeous, of course."
"I'll take that as a compliment, Kyle, but just remember under this
flimsy little dress is a guy and a guy who has no interest in men."
"No interest in men? So why do you dress like that?"
"Because I like it. It's great fun and I'm immodest enough to think I'm
pretty good at it. I love seeing the effect I have on men."
"But you said you have no interest in men."
"You're right, Kyle. No interest romantically," said Katie. "But I
don't need to fancy them to like the reaction. Did you look at my tits
or my legs first?"
"I don't know. I guess your tits. They are lovely. That's a very
realistic cleavage. Are you on hormones or anything?"
"No the tits aren't real. I use something called a nu-bra to create a
cleavage and slip a pair of silicon breast forms into the cups of my bra
to get the shape. Some girls take hormones - it gives them tits but it
means they can't do what men do."
Kyle wondered exactly what Katie meant but he didn't ask. "Your legs are
great too, Katie."
"Thank you but remember there is more to a girl than her tits and her
legs."
The kitchen door opened and in came Hannah carrying a bottle and Simone
carrying four glasses of wine. "You two seem to be getting on all
right," said Hannah. "What were you talking about?"
Kyle looked embarrassed. Should he reveal the truth? He decided that
sometimes the truth is easier. "Tits," he said. "We were talking about
tits. And legs."
"Well at least you weren't talking about, football, Formula 1 or the
price of beer," Simone said.
"Katie would never talk about football, Formula 1 or the price of beer,"
Hannah said. "She's much too girly. She likes to talk about fashion;
girly dresses, floral tops, frilly undies, cosmetics, handbags and
shoes, don't you Katie?"
Katie nodded. Simone handed round the wine starting with Katie. "Ladies
first, she said.
"Cheers," they all said.
"Here's to a fun packed evening," said Hannah.
Sitting opposite Kyle, Katie wondered if he could see her pink panties.
He couldn't but not for the lack of trying. He found it hard not to look
at Katie's thighs.
Then Hannah announced the food was ready and they all went into the
kitchen. Kyle sat opposite Katie again. He could no longer see Katie's
thighs but a few times he found himself staring at Katie's cleavage.
Katie felt a little awkward with her friend staring at her like that. At
the end of the meal, Hannah offered her guests coffee.
Katie said, "I need to powder my nose."
She stood up and headed for the stairs. Hannah and Simone assumed that
she was going to repair her lipstick. In fact Katie headed for the spare
room. She kicked off the court shoes, took off the wig and then peeled
off the leopard print dress.
She put on a baby pink, chiffon, princess dress. It was short sleeved
with an 'Empire' waist line. It was decorated with lots of ruffles. It
was very girly and very short - much shorter than the leopard print
dress. It barely hid Katie's pink panties. She then put on a pair of
strappy silver shoes with a 4 inch heel. She put a row of beads around
her neck. She put on a curly blonde shoulder length wig and brushed it.
Finally she redid her lipstick. Katie could hear noises from downstairs
which suggested they were all in the lounge drinking their coffee.
She carefully tottered down the stairs and into the lounge. Hannah was
just about to say, "Where have you been?" when she realised she knew
exactly where Katie had been
"What a great dress," Simone gushed. "It really shows off your figure
and legs."
"Yes it's great," said Kyle.
Hannah said nothing. She thought the dress too short and too young for
Katie. It was very girly and more suitable for a twelve year old. Katie
of course disagreed. For now Hannah said nothing but Katie knew from the
look on Hannah's face that she would be having 'words' later.
"We've decided to play 'Highest and Lowest'," Simone announced.
"'Highest and Lowest'?" queried Katie. She had never heard of it.
"It's an old swinger' game," explained Simone. 'How does she know about
swingers' games,' Katie wondered.
"We each cut a card," explained Hannah. "The person with the highest
card and the person with the highest card then have to kiss. For at
least one minute. Aces low. Two cards the same, cut again. OK?"
Suddenly it dawned on Katie that this was not like postman's knock where
girls only kissed boys. He might have to kiss Kyle. "I'm - er - not sure
that ..." he stammered.
"Oh nonsense, Katie. You'll love it. You know you will. I've got a pack
of cards here," said Hannah. Kyle looked like he was looking forward to
it.
She shuffled the cards and put them on the coffee table. All four cut a
card and kept it secret. Then they all called their scores out.
Kyle: "10 of Clubs."
Hannah: "9 of Hearts."
Simone: "6 of Spades."
Katie with some relief, "9 of Spades." The highest was Kyle. The lowest
was his wife Simone. They both stood up, wrapped their arms round each
other and enjoyed a long sensuous kiss.
Hannah shuffled the cards again. "OK time's up," she called when Kyle
and Simone showed no sign of stopping. Eventually they finished and sat
down.
"Round two," said Hannah. They all cut again and called out their card.
Kyle: "9 of Diamonds."
Hannah: "2 of Diamonds."
Simone: "4 of Clubs."
Katie again with some relief, "4 of Hearts."
The highest was again Kyle. The lowest this time was Katie's wife
Hannah. Hannah and Kyle had been close in their youth before Jack had
started seeing Hannah. Kyle was going to enjoy this. As before the two
winners stood up and kissed sensuously while Kyle's wife Simone and
Hannah's husband Katie looked on. Katie fund that watching his wife
kissing another man was very sexy. She looked away and shuffled the
cards.
After a minute or so the kiss broke off. Kyle sat down in the armchair
opposite Katie. Hannah sat down on the settee next to Simone.
"Round three," said Katie hoping it might be the last round. In turn
they reached across to the coffee table, cut again and called out their
card.
Kyle: "7 of Clubs."
Hannah: "8 of Spades."
Simone: "Ace of Hearts."
Katie "Queen of Diamonds."
The lowest this time was Simone, the highest Katie. Simone in her sexy
black and white dress stood up again. Katie in her girly pink dress also
stood up and minced over to Simone in her killer heels. Simone in her
sexy, short black and white print dress stood up too.
The two met in a hug and their lips brushed. Suddenly the kiss became
intense and affectionate. Somehow Simone's hand had got up Katie's
dress. Then Katie hitched up Simone's dress at the back. She had pulled
down Simone's tights and was massaging her ass.
To Katie it felt like the best kiss she's ever had, made more sensual by
the occasion - her coming out and the fact that her wife Hannah was
watching the kiss. They kissed for three maybe four minutes before
separating.
"It looks like Katie enjoyed that," said Kyle pointing to a large bulge
at the front of Katie's dress.
Katie sat down a little ashamed. Simone sat back down nxt to Hannah.
Hannah had shuffled the cards again. "Fourth and last round," she called
and they all cut and again called out their card.
Kyle: "9 of Hearts."
Hannah: "8 of Hearts."
Simone: "6 of Spades."
Katie with some trepidation, "3 of Clubs."
The lowest this time was Katie, the highest Kyle. Hannah was
disappointed and said out loud, "I was hoping for a little snog with
Simone." Katie was disappointed too, in fact it was Katie's worst
nightmare as she would have to snog Kyle, a man with a wandering eye and
wandering hands.
Kyle was delighted to get his third kiss out of four and was going to
kiss the pretty Katie. Resigned to the fact that she would have to kiss
a man, Katie said to herself, 'Let's get this thing over.' Life as Katie
isn't always a bed of roses.
Katie stood up in her heels and walked over to Kyle who was sitting in
an armchair. Katie sat in Kyle's lap, sitting across Kyle. To Hannah and
Simone Katie's thin legs looked longer than ever. Her girly dress rode
up a little more.
Kyle thought she looked cute. Katie tried to be calm and not reveal that
she was more than a little anxious. Kyle put his arms round her. Katie
turned to face him and leaned forward so that their lips met. Kyle now
had his hands locked around Katie's waist and he pulled Katie even
closer towards him. His manhood rubbed against Katie's ass. Soon they
were kissing, hungrily, longingly, lustfully. Katie had never kissed a
man before. She had never felt the roughness of a man's bristles against
her delicate cheeks.
Kyle had never kissed a man before either. Although Katie had shaved
closely, Kyle felt the Katie's bristles against him. Katie let his
tongue enter her mouth. The electricity between them seemed as if sparks
were about to fly. Hannah and Simone, sitting next to one another on the
settee looked on entranced. It was clear that Katie was enjoying it.
After about two minutes of Kyle and Katie kissing, Hannah pulled Simone
towards her and started to kiss her. There was an exciting chemistry
between them. Neither of them knew where this would lead but they didn't
care. Hannah opened one eye and stole a look at her husband in the pink
dress.
Somehow Katie's tights and pink panties were down around her knees. The
kiss was energetic and sexy. 'She's always says she has no interest in
men. It doesn't look that way, the little slut,' thought Hannah before
she remembered she was kissing her best friend and stroking her breasts.
'Am I a slut too?' she wondered. She shut her eyes and concentrated on
the kiss with Simone.
Now Simone had her hand up Hannah's vintage floral print dress. Hannah
didn't care. Well in truth she did care because she was enjoying herself
so much. Simone had Hannah's panties in her hand, a little tug and the
delicate panties tore and came away in Simone's hand with her tights.
And still they kissed. Now Simone had her finger in Hannah's sex. It
felt delightful. Hannah could only reciprocate. She put a hand up
Simone's black and white mini dress and started to massage Simone's
thighs. Simone's panties also were insubstantial. A little pull and they
and her tights too gave away. Within a few seconds Hannah was massaging
Simone's vagina.
Hannah stole another look at Katie kissing Kyle. Katie's tights and pink
panties were down around her ankles. Her pink dress had got rucked up
and Katie seemed naked from ankles to waist.' Is Kyle masturbating
Katie?' wondered Hannah. 'She is a slut,' Hannah thought as she was
kissed Simone.
No one knew how long that kiss lasted. It might have been 20 minutes or
maybe half an hour. They suspected that it was closer to one hour
before, very out-of-breath, the two couples separated. Hannah and Simone
with their shredded panties and tights around their ankles, providing
evidence as to what had gone on. Katie had kicked her sandals off, her
tights were bedraggled across the floor, her dress all hitched up and a
little torn at the neck. And she had a massive hard on.
Any embarrassment at what had happened was more than compensated by the
enjoyment that they had had. Katie pulled her dress down to hide her
penis and then pulled up her panties. There was a damp stain on her
dress at the front. Was that her or Kyle? Hannah was still stroking
Simone's thighs lovingly. Simone was pleasuring herself with her finger.
Katie started gently kissing Kyle's neck and Kyle once more seized the
opportunity by feeling up Katie's dress.
"Well," said Hannah. "What are we going to do now?"
To be continued?
Vicky
- 13.06.2020
- 8
- 0
