Tara s Bayou Level 1 Fresh Meat
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Heads You Dress......Chapter Three free porn video
CHAPTER THREE --- THE BRA FITTING & THE FIRST DREAM
1
They arrived at the shopping mall about half an hour after Debs had
picked up Jason from his office.
"Other trips will be more fun," Debs assured him. "But for now, Jenny,
I'd just like you to do as I say."
Jason nodded. He accepted after the events earlier in the day with Kelly
that he'd be addressed by the feminine name. He also wondered if this was
about more than wearing women's panties as he originally thought.
"Why are you doing this to me?" he asked as they crossed the parking lot.
She smiled. "You know why. But I have a better question: why are you
letting me do this to you?"
He was about to answer, but she placed a soft finger on his lips,
wondering what his instinctive answer might have been.
"Not yet. Think about it. Maybe tell me in a few months."
"Months?" he protested. "How long are we going to play this game?"
"Who said it was a game?"
They entered the mall, Jason more unsure than ever about what was
happening. He was on a rollercoaster, blind-folded, and didn't know where
the next dip or dive would be. And, yet, at this moment, with his wife at
his side, he could feel her....compassion. He didn't know what her
endgame was but he was sure she had his back when poush came to shove,
that he wouldn't be hurt.
She pointed across the walkway to Boux Avenue and he started to drag his
feet.
"Look," Debs explained as they reached the entrance, "after all Kelly did
to you today I've decided to rip the masculine band-aid off. You've
handled things so well. You're more accepting of this than I ever
imagined you would be."
He paced near the door, stepping aside for a couple of women.
"Here," she said, handing him her compact. "Just touch up your lipstick
and we'll get shopping."
Jason popped open the small mirror and removed his pink lipstick. He
carefully applied the delicate colour on his lips.
"Just one more coat, Jenny," Debs instructed. "And don't forget your
gloss."
2
Inside the store, they spent a few minutes browsing before a woman
approached. She was middle-aged, good looking. Her name tag read Carol.
"You must be Jenny," she said as Debs held a lacey balconette up to
Jason's chest.
He was speechless.
"It's okay," the woman said. "My name's Carol. I'm the manager here. Your
wife said you might be shy when she called ahead. No need for that, dear.
Do you see anything you like?"
"I-it's-what's-"
"Baby," Debs began, "when I said we were getting your first bra you
didn't think we were just going to grab one off the rack, did you?"
"I don't-it's just-" Jason stammered.
Carol placed a hand on his shoulder.
"It's okay, dear. I'm going to look after you, and we are going to find
you a wonderful bra or two. But first thing's first. We need to find out
your size. Follow me."
Debs followed the manager. Jason stood still, dumb-founded.
His wife looked back across the sales-floor, women and couples now
between them.
"Come on, Jenny. Time for your bra fitting."
The other customers, nudging each other with a giggle or two, watched
him, red faced, enter the private fitting area.
3
"Take your top off," Carol instructed.
Jason barely reacted. He looked at Debs. "Is this for real?"
"She does want this, doesn't she?" Carol asked Debs. "I can see she's
wearing lipstick. You said on the phone this was serious, but she
seems....reticent, to say the least."
She? Jason almost blurted out, wanting to remind the manager he was a
man. But Debs caught his eye. It wasn't stern or severe, but
compassionate. Was it a trick? Jason thought. Was she playing good cop to
Kelly's bad cop in the office? Or was she genuinely nurturing him through
the changes she was imposing on his life?
Here was a chance for escape, if he wanted it. He'd probably be
humiliated for his trouble, but what could be worse than this? Finally,
it wasn't fear that drew him to the conclusion he reached. It
was....curiosity. Longing. He'd worn panties on and off all his life, and
now his wife was pushing him into beautiful, unexplored feminine
territory. What did that mean, that his resistance was so low?
"Well, Jenny?" Debs asked.
Jason nodded. He removed his top. He wasn't in bad shape, but he was
definitely on the wrong side of letting himself go. He wasn't ashamed of
his body, but it had seen better days.
"Okay, sorry for the cold hands," Carol said, briskly rubbing her palms
together. She measured around his body with a tape measure, considering
his shape. "She looks like a natural B-cup."
"I am not," Jason protested.
Carol checked. "Definite 38-B."
For a few seconds she held his small, pert mounds. Jason tried not to get
hard. Debs suppressed a small laugh at the unintentionally awkward
moment.
"No," he repeated. "I don't have breasts."
Carol looked at Debs. "I'd recommend inserts all the time. She has a
nice, natural roundness and they'll help her shape develop."
"I don't want-" Jason began.
"Hush, now, Jenny," Debs said, holding her hand up. "This is important
advice. Even while she's sleeping?"
"Typically, no. I'd strongly advise against wearing a bra to sleep,"
Carol said. "But in this case, it will help her develop naturally."
"But I'm not a B-cup," he protested.
"Well, dear, with padding and inserts you can be any cup size you'd
like," Carol explained.
"C?" Debs asked.
"Sure. The actual size of the cup might be too big for her body, though.
A B-cup would definitely be a beter fit for her." She looked to Jenny.
"If you ever get true with this situation, there's obviously hormones to
enhance your look, surgery..."
"What-?" Jason began.
"Look, dear. I'm not one to judge. You can have any breast size you
like."
Jason started to panic.
"Relax, Princess," Debs assured her, holding her hand.
"But I just want to be a B-cup," he said, hoping to appease them. "I
don't want everyone staring at my big boobs."
"Then a B-cup it is," Debs said.
"Good. Can I go now," Jason said, reaching for his top.
Carol laughed good naturedly. "Jenny, you'll get used to this, but most
women's sizes are not standard. They vary from manufacturer to
manufacturer, from style to style. Whenever you buy anything, always try
it on first to see if it looks good on you. Starting right now."
4
Jason waited while Carol and Debs discussed what styles and colours might
suit Jenny on the salesfloor. They returned with several options and he
had to try each on. Carol adjusted straps and ensured a good fit and they
then considered how he looked.
"I like this one," Jason suddenly said, surprising them both.
Debs smiled sweetly as Carol said: "This is fantastic. Now we know you're
going to have an opinion, let's grab a cute little balconette."
When Carol left the booth, Debs kissed him. It was a warm moment. "If
this wasn't supposed to be a punishment, I'd let you have me right now."
"Punishment?" he asked. "What for? What did I do?"
"Stop playing stupid. My friend told me how you made a pass at her. That
you were using our real estate business as a chance to meet women."
"I sell houses. Of course, I flirt with women now and then. The same
reason I talk sports and movies with the guys."
"I'm not only talking about flirting," Debs chastised him.
Carol knocked on the door. "Everybody decent?"
She entered and handed him a white balconette, with a black striping
creating a panel effect.
"It's gorgeous," he gasped, not quite sure why. But it really was pretty.
He removed the bra he was wearing, unclasping it behind his back.
"You're getting good," Carol noted.
Debs watched as he fastened the new bra. She had almost told him why this
was happening. As a punishment for cheating on her. She shut the thoughts
out and decided she would not slip like that again. She knew the mystery
of why she was feminising him was driving him crazy. That was as much
part of the punishment as what they were doing to him.
Carol opened a pack of inserts and helped him position them, his shape
changing ever so slightly, the roundness at the cleavage area increasing.
Jason smiled at his reflection.
"That style really suits you," Carol told him.
"Thank you."
"We'd like matching panties for that one," Debs said to Carol, "and these
three. You decide the style. Can she wear that one to go?"
"No problems," Carol said.
"With the inserts," Debs asserted, still angry at herself.
When Jason protested, she hushed him. "You'll need the bra so I can see
how the blouses will look."
"Blouses?" he gulped.
5
At the checkout, Carol began to ring through his purchases. A couple
nearby sniggered, having seen the man emerge from the fitting room,
obviously wearing a bra under his shirt.
"Ignore them," she whispered. "You did great."
"Thank you," Jason said. "You were very kind and helpful."
"You're welcome, Jenny."
He looked at Debs, wanting to ask something. "Well, don't be shy," his
wife said.
"May I....Can I visit here again for my lingerie?" he asked.
Debs smiled happily and considered Carol.
"Of course, dear," Carol said. "When you begin dressing more-"
"More?"
"Yes, you know, in a skirt or a dress, I'd like you to present as a
woman. I'd love to see you."
"That's not happening anytime soon."
This time Debs' smile was more secret, but Carol picked up on a glint in
her eye. She reached over and touched his arm. "Anytime you are dressed,
just pop in. But if you are wearing these horrible male clothes, call
first so I know that you are on your way. I've got an idea. Why don't I
set you up with your very own Boux Avenue loyalty card?"
Jason looked to Debs, taken by the moment.
"Can I?"
"Of course, Jenny,"
So he remained at the counter for another five minutes, delighted with
his purchases, filling in a loyalty card application.
"It's a nice pink card," Carol said when he had finished. "Watch out for
it in the post in the next week or so."
6
They then shopped at various women's clothing stores. She held several
blouses up to him and made enquiries about different pairs of trousers.
When a sales clerk approached and asked what they were looking for, Debs
explained they were after a mixture of blouses, ranging from plain and
neutral to sexy and patterned, and several pairs of trousers.
"But the zipper must be at the side or the rear," she said.
The sales clerk considered Debs. "You look about a-"
"Oh, no. They're not for me. Jenny here is just starting her wardrobe."
Jason blushed red as the clerk considered him with a humorous smile.
Debs explained her needs in the different stores and the clerks all had a
similar reaction: gentle amusement, but happily helping. So in each one
Jason had to try on different outfits, mixing and matching the clothes.
Each time he had to step out of his cubicle praying that nobody would see
him. His wife and the sales clerk helping them would comment on how he
looked, and if the clothes worked, making adjustments and discussing
options. He was so embarrassed, standing there for all to see, face red.
Other customers smiled and laughed and tried to contain their giggles.
"He certainly doesn't need any blush," one of the sales clerks joked.
After an hour or so they had three blouses and three pairs of trousers.
He considered their fit. Snug on his hips and flared at the bottom. No
way they were going to pass as men's trousers. But that didn't matter,
because the blouses he would be wearing --- from the buttons on backwards
to their soft material and shape --- didn't look like shirts, anyway.
7
"One last stop," Debs said.
"Can't we go home?" he whined, aware of how daft he looked. Not only had
Debs made him wear a bra from the store; she had also insisted he wear
one of the blouses and trousers. Which zipped in the rear. Whose idea was
that, anyway?
He was aware of the slight bulge in the front because his body was not
designed for the cut of the material.
"Don't worry. We can tuck your clittie between your legs," Debs assured
him. "Especially at times like now."
"What times?"
She punched his arm playfully. "When you're on your period, silly."
They reached Clarks, a shoe shop.
"This is why you had to wear the trousers. So we can see how the shoes
look."
"I'm not wearing high heels," he protested instantly.
"Come on inside. There's lots to choose from."
There were several pairs that fit. They were restricted by size and the
sales clerk also noted he would need a wide-fitting shoe. Debs had him
try the options on, and to walk around the store in them, again to the
amusement of other customers. Debs settled on a couple of pairs of medium
heeled court shoes. One had a black strap decorated with tiny stones. It
was so cute.
At the check-out the clerk considered him. "Which would you like to wear
out?"
"I-But-"
Debs laughed. "Come on, Jenny. Don't be a spoil sport."
"The black ones," he confessed, drawn to the shiny straps.
"They're so girlie," the clerk smiled, handing them over. She looked at
Debs. "When he's ready for some real heels order them in on the website
and bring him in to try them on a day or so later."
She considered Jason, just fastening the straps. "I just love high
heels," she said. "Don't you?"
Jason looked up and could only blush.
"I've never worn them," he said.
"Yet," Debs interjected.
"You're in for a treat," the sales clerk smiled.
7
When they returned home Debs instructed Jason to shave.
"From now on, you'll shave every morning. And not just your face..."
Reluctantly, he ran the bath, enjoying the scent of the bubbles as he
tried to access a feminine frame of mind. This was happening. For
whatever reason his resistance levels were low. Truth be told, except for
the public humiliations, he was enjoying exploring this side of his
personality, and considered himself extremely lucky that Debs was helping
him. Even if she did have her own motivations.
He set up his pink razors and women's shaving cream ready and stepped
into the bath. He soaked for a while and then, with a deep breath, began
to shave. First his legs, then his armpits. Why stop there? This was
liberating in a way and he imagined how much better he would look in the
clothes without hair. He shaved down his arms and then his chest and
tummy. It was then he reached his private area and was a little unsure
what was expected of him.
"Debs!" he hollered.
She entered the bathroom, unsure of his progress because of the bubbles.
"What do you...? Downstairs?"
"What are you talking about?"
"My...you know....."
"Oh, stop being all shy about your clittie."
She reached into the bath and tucked it between his legs. "Look."
He glanced down. Jesus. It looked like he had a pussy.
"I want all this hair gone, and then I think you should shape what's left
into a tiny little heart to represent how much you love what I'm doing to
you."
She grinned. Even if he did flirt while wearing women's clothing, if one
of his floosies was tempted by him, they'd surely fail to be impressed
when they saw his feminised and heart shaped pubic area.
"That will look-"
"Well, it's that, or I could look into getting that area waxed."
"No, no," he quickly said. And set to work, removing the last of his hair
except for the tiny heart shape that sat above his.....clittie, he
thought, his stomach twisting into a knot.
"Good girl," Debs grinned. "Don't forget to moisturise all over. Day and
night from now on."
8
When he entered the bedroom he found two gift boxes waiting for him.
"I got you a little treat while we were in Boux," Debs explained. "Go on.
Open them."
Inside the first he found a gift card for the lingerie store.
Debs smiled. "I've loaded it with a hundred pounds for you."
"Thank you," he said hesitantly.
He opened the second box and carefully unfolded the crepe paper. He then
held up a gorgeous nightie. It was long, with heavily laced slits to show
some leg and lace trimming around the cups; the straps were narrow and
decorated with bows on the shoulder, before they criss-crossed down the
back.
"Do you like it?" she asked.
"It's beautiful. But shouldn't you-"
"No, silly. It's for you. Try it on."
He reached to put it over his shoulders.
"Wait," she called. "Don't forget these."
She held out a pink bra with inserts to help his shape.
"I can't really sleep wearing-"
"Remember what Carol said. They'll help your shape."
"But-"
"Put them on, Jenny."
He hooked his arms through the bra and she clapped with delight when he
fastened the clasp behind his back. He carefully slipped the inserts
inside, positioning them best to enhance his shape and create some
cleavage.
"You look good," she smiled. "Especially smooth. Now these."
From under the covers she held out a pair of pink satin panties and a
panty-liner.
"But-"
"Kelly is setting up your period tracker, but since it only just started
I imagine you've got at least a few days and nights left."
"I don't want to have a period."
"Jenny, remember, just because you seem to be finding some pleasure in
what we're doing, you don't actually have a choice. Now, I think you
should experience, if only to a tiny degree, the discomforts that come
with being a woman. It's not all about sexy clothes and pretty lipstick."
He thought about running from this. Considered seriously filing for
divorce. But he had always loved wearing panties, and what was happening
was only an extension to that. It didn't mean anything, did it?
He positioned the panty-liner and pulled the panties on.
"Thank you," Debs said.
Then, finally, he tried on the nightie. The bra created a nice look and
he pushed his bust out a little.
"If I wasn't so angered by what you did, I'd take you right now, Missy."
"Then let's-"
"No," she held up her hand. "Not for a while, anyway. I need to learn how
to forgive you."
"Forgive me? For what? Firting to close deals?"
"Come to bed and-"
"No, I want to talk about this."
"Are you happy I'm doing it?" Debs asked.
Jason considered the question. If he wasn't happy he'd certainly be
fighting it a whole lot more. Talk of periods and the stuff Kelly was
doing was a bit much, but...
"Well?"
"I think so," he confessed.
"Then try to sleep. You're probably going to be restless and tomorrow is
your first day in work wearing one of your new outfits-"
"Debs, don't do that. I'll wear them around the house for you, but-"
"But, but, but......Goodnight, Jenny," Debs said and was asleep in
minutes.
9
It took Jason a while longer. He was excited by what was happening. Hard,
even though his penis......his clittie......was tucked between his legs.
That actually didn't help, his thighs rubbing on it. Even with the window
open, he was hot in the lingerie and nightie.
Eventually, despite the tossing and turning, sleep found him.....
Only a boy, probably five or six, Jason waited until his parents left for
a night out. Then, when the baby-sitter thought he was asleep, he snuck
into the bathroom. He rummaged until he found a pair of his mother's
panties in the dirty laundry hamper and, checking like a spy to be sure
he wasn't seen, he slipped them on.
The soft material felt so good on him, so right. He crossed the hallway
and went into his parent's bedroom, began to open drawers until he found
the one where his mother kept her underwear. The secrets it held.....the
fabrics so soft, the lace so gentle. He caressed the underwear against
his cheek, his skin. It felt so marvellous, so much nicer than the
horrible boy clothes he had to wear. He wished he could wear the clothes
all over, be wrapped in silk and satin. He didn't understand what was
happening.
Memories merged with the dream and he was older now, about ten, still
wearing his mother's underwear whenever he could. He was careful, never
caught, and he sometimes wished she knew, that she sat him down and told
him there was no need to hide or feel guilt, no need to be embarrassed,
and that if he wanted to wear women's underwear she would make sure his
father understood. How wonderful it would be to not have to hide all the
time.
He could even wear them to school, if he liked, she would tell him. That
would be so perfect. Cut to school and the girls were laughing at him,
pointing and giggling as they taunted him about clothes and make-up; some
even pinning him down to decorate his face with lipstick and mascara-
"No, no...." he cried in his sleep, bolting up in a feverish sweat.
Debs rolled over. "What is it?"
"Just a dream. A very bad dream. Some of the stuff happened. Some of it
didn't. It was scary, though."
"But you enjoyed it, too," she said, touching his wet thigh where a small
amount of cum had escaped his panty-liner.
"I didn't mean to," he said. "It just seemed so real. I better change my
panty-liner."
He started to get from the bed, but she held him back.
"Jenny, I loved the way you said that, your natural thought process and
instinct kicking in, but come to bed."
"It's sticky," he said, his slowly shrinking penis drenched in cum.
"A period is going to be uncomfortable," she whispered as he settled
down. "Get used to it, Jenny."
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