Hero in Heels Part One
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Hero In Heels Part Two free porn video
Part 5: Practicalities
At long last Charles heard a key rattling in the apartment door,
signalling Dorothy's return. She walked into their small office with
several bags and a big grin when she saw Charles.
"Good choice!" she complimented him. "That colour goes well with your
hair."
"Erm, thanks," he said, not sure how to take the praise.
"You've freshened your lipstick too," she said, looking more closely.
"How can you tell?" he asked in a strained voice, even more disconcerted
now.
"It's a girl thing," she smiled. "Don't worry you did a great job. You
always were a quick learner. Which is just as well; you've got a lot to
learn if we are going to make this work."
He looked down at her bags and asked in surprise, "How much stuff did you
buy? It's not like I'm considering doing this twenty-four-seven."
She shrugged as she glanced at the spoils of her day. "Hey, even this
much was hard. I've had to try to find a range of things to match your
frame and colouring without you there to try them on. We'll be lucky if
half of these work - the rest I'll return to the stores next week."
He laughed. "Well, there's no way I could come along for a fitting, so
that makes sense I guess."
She gave him an odd look, and her head tilted to one side, with a little
smile, then turned and headed out of the room saying, "I'll leave these
on the bed. When you're finished we'll see how well my guesses worked
out. I'll make us some lunch while you're still working."
Half an hour later he sent out his last email and walked through to the
kitchen. Dorothy had prepared a salad, and unusually poured a couple of
glasses of rose wine to accompany it. The table was by a small window
that looked out onto the street which was open wide to let in the late
spring air.
He hesitated. "Um, I'm not sure that's a good idea, someone may be able
to see me."
"Oh, don't worry," she giggled, "we're on the third floor. As long as you
don't lean out of the window no one in the street can see you."
"What about across the street?"
"That's the old couple. They'd be lucky to see each other, let alone us;
and even if they did, they'd only be able to make out a couple of ladies
lunching."
"All right, I suppose," he said, somewhat mollified, and sat down. "Why
the wine? Not that I'm complaining of course."
"I thought it would take the edge off before our little fashion show. Oh,
and to welcome my new girlfriend." She picked up her glass and toasted,
"To new experiences!"
He tapped his glass to hers with a ting and smiled. "New experiences!"
They chatted over lunch, and once again he began to forget about the wig
and makeup. The wine probably helped, and Dorothy noticed that he was
making feminine gestures as he got into this girl-thing. They had a
second glass of wine before they knew it. Charles was about to pour a
third, when Dorothy stopped him.
"How about I get things ready while you clean up?" She stood and the
picked up the glasses and half full wine bottle and headed off in the
direction of their bedroom.
Charles was feeling the pleasant glow and began to clear up the table
when he spotted Dorothy's apron that she used when cooking. He slipped it
over his blonde head, and then tied the waist ribbon behind his back with
difficulty into a large, floppy bow. Suitably armoured for combat, he
attacked the dishes and bowls, hand washing and drying them, before
cleaning all the surfaces and tidying the kitchen in general. He was
absorbed in the task, and it wasn't until he put away the final item
under the sink that he noticed Dorothy was leaning her shoulder on the
door frame and watching him with that same strange expression.
He was again, a little flustered and embarrassed. "Just getting into
character," he said, rapidly taking off the apron.
Dorothy could see that despite the wine, he was getting worried, so she
quickly walked over to him and gave him a hug. Then, holding his shoulder
she looked up into his eyes, "Charles, I love you, and no matter what you
wear or how you act, that won't change. I'm so relieved that you have
agreed to try this out, and I can tell how much you love me that you're
willing to do it in the first place." Then she pulled him towards her and
clamped their painted lips together for a deep and lingering kiss.
Finally, they came up for air and again stared into each other's eyes;
she winked. "And if it also means that I get extra help in the kitchen
then this is a win-win situation for me."
Much more relaxed, Charles followed Dorothy into their bedroom, to
discover a variety of colourful items spread across the bed.
"OK, let's try this one first," said Dorothy, holding up a lilac and red
patterned blouse. Charles unbuttoned his shirt, draped it over the back
of a chair before standing in front of Dorothy bare chested. His Scottish
ancestry had gifted him a fair amount of body hair and he had considered
it his Sean Connery look, although he now noticed a little grey was
beginning to appear.
Dorothy pursed her lips a little at the sight but said nothing. She
handed him the garment and instructed, "OK, slip this over your head like
you're putting on a sweater." He struggled a little as there wasn't so
much stretch in the material, but finally his arms and head popped
through. She then fussed around behind him, apparently doing up some
buttons. The sleeves seemed a little short to Charles, but when Dorothy
stepped around and did up the three buttons on each cuff she seemed
satisfied with the fit.
Something was still bothering her though. "Turn around. Walk over there
and back. Hmmm."
Charles did as he was instructed. The blouse felt nothing like any male
garment he was used to. It was much more closely cut, fitted to his body
shape. It was made of a silky material that slid across his skin but had
little give, so he felt almost constrained. He was also pretty sure he
wouldn't be able to reach the buttons at the back, so he was trapped
unless Dorothy helped him. He shivered at this, but also felt a strange
thrill run through him and his skin prickled with goose-bumps.
At last Dorothy said, "OK, I was afraid of this."
"What's wrong?" asked Charles, jerked out of his reverie.
"It doesn't hand right on your chest. The rest is fine, but you will need
a little padding there I'm afraid."
Charles gulped. "Um, are we talking breasts here?"
"Well you've always said how much you liked mine," joked Dorothy, "Now's
the time to try them for yourself," She stepped behind him and he had a
little trickle of disappointment as he felt her begin unbuttoning the
blouse. He tried to help a little with the cuff buttons, but through lack
of practice the little pearl fastenings tended to elude his fingers.
Moments later she slipped the light garment over his head and he once
more was bare chested.
Dorothy fingered his chest hair and not looking at him said tentatively,
"I know I said only the beard needed to go, but..."
Charles sighed. "OK, in for a penny. But you may have to help me a little
with this"
Once again, he found himself shaving in the bathroom mirror, but this
time it was a completely new experience. He lathered his chest and began
to clear what had been his mark of masculinity since he was seventeen.
Stroke by stroke it vanished as if something fundamental was being
stripped away.
Behind him Dorothy carried out a similar process on his back. There was
far less hair, before she instructed him to hold up first his left then
his right arm as she shaved his armpits bare. His arms were next, and
after wiping him down and drying off with a fresh fluffy towel he stood
in front of her feeling more naked than he did when they made love.
This skin had never been shaved, so now it was sensitive and almost raw.
He flinched a little when she touched him, so she opened one of the
mirrored cupboards where she kept a wide variety of mysterious feminine
products and retrieved a bottle of pink lotion. She carefully and
somewhat sensually smoothed the floral scented substance over his torso
and down his arms. This quickly soothed his abused flesh, and rapidly
began to arouse him.
She patted his obviously excited crotch and kissed hi briefly on his now
smooth chest and said, "Not yet tiger, we've got some serious modelling
to do first." She took him be the hand and led him back into their
bedroom.
"OK, you're pretty efficient a taking off bras, let's see how good you
are at putting them on." She handed him a simple white, lace-trimmed item
that was obviously new as she had to first remove the tag. It was a
different experience trying to work out how all the loops and clips lined
up, but after some fiddling Charles managed to slip the shoulder straps
up his arms. The chest strap was even more complicated until he found a
way to slide his hands along the elasticated band and slowly pull the
cups into place. With his hands behind him there was more mind-bending
visualisation as he tried to picture how the tiny hooks and eyes could
match up.
Dorothy grinned as she circled him, and finally guided his fingers to
complete the process. "That was very good for a first time," she
congratulated him, "I was worried you would connect the strap at your
waist then spin it around, but you went for the proper elegant way like a
champ."
Charles thought, "Damn, that never occurred to me," but he said, "Just
following your lead I suppose my darling."
The bra was another entirely new feeling for Charles. The tight strap
around his smooth chest, with the thin shoulder-straps that Dorothy was
adjusting to her satisfaction, the soft, empty cups covering his nipples.
No male garment was remotely similar.
"OK, next step," said Dorothy, now satisfied that the cups were correctly
positioned. To Charles's surprise, she slipped her hand into first one
cup then the other, reaching under the chest band and pulled up his
hairless flesh to make small mounds. "This is a push-up style of bra, it
helps enhance your natural attributes; and talking of enhancement..." She
picked up another packet from the bed and extracted a strange rubbery
looking item. "This is a 'chicken-fillet', it's used to give the less
well-endowed girls - like you - a little more help when they need it."
Grinning she tucked these under his mounded flesh and pushed things
around a little more.
Finally, she stepped back and said, "Well, what do you think?"
Charles looked down, he jaw a little slack, then wordlessly we moved
across to the full length mirror in the corner. "I can't believe it."
Rising from his chest were two, small but convincing breasts, seemingly
bulging out of his - a weird thought on its own - bra. He poked one with
a finger and it moved convincingly. He could feel the additional weight
provided by the inserts, and after a moment he playfully shook them from
side to side and watched them swing and bounce just like the real thing.
He quoted an old Billy Connelly joke, "Well now I'll be able to stay home
evenings!"
Dorothy laughed. "I'm glad you like them."
She handed him a blouse, a different one this time, floral, with gauzy
sleeves. When he slipped it over his head and settled it over his new
breasts he found the neckline was very low, showing off his smooth chest
and some of his brand-new cleavage. This became even more well defined
when Dorothy buttoned up the back of the blouse and it pulled more
tightly over his new curves.
"Yes, much better," she said, "and one final touch for your ...
disguise."
Dorothy unclipped a small case then slipped onto his face a pair of very
feminine, but business-like glasses. "They're reactive sunglasses, so
they will be clear when you're inside."
Charles turned back to the mirror, and Dorothy stood on tiptoes to look
over his shoulder. Now he did not recognise himself at all. Two pretty
women looked back at him, one petite with long, tousled, sexy hair, the
other a tall sensible blond in a pretty revealing top; perhaps an
accountant with a flirtatious side.
"What do you think?" asked Dorothy, when the silence had stretched a
little too long.
"I think this will work," he responded in awed tones.
One of Dorothy's manicured hands slipped up to cup his breast through the
silky material of the blouse. "I think so too," she purred. Her other
hand slid down to his bulging crotch, "and there's certainly some side
benefits."
Then she laughed and slapped his crotch playfully. "But not just now!
We're not finished yet; fashion is a serious business you know," and she
immediately started to unbutton his blouse.
Ultimately, he tried on nine different blouses and tops and selected five
to keep. Of the four that Dorothy put aside to return there were three
that she felt didn't really flatter his new body shape, and, most
surprising to her, one that Charles rejected. He was a little reticent
about explaining why, but she got the impression that he didn't like the
style when he saw it on himself; it didn't suit the character that was
being created - or maybe discovered.
Elissa
- 14.04.2022
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