The Housekeeper
By Karen Singer
Chapter 32 Part 3 of 3
“Roger,” Jennifer stated flatly,
“I’m not going to pick out a dress for you!
You’re going to have to look and find what you like yourself. I’m more than willing to let you know what I
think about it, but you’re going to have to shop for yourself!”
“I’m trying,” Roger replied. “I
just don’t know… what to look for.”
“A dress! You’ve got a whole store full of them to
choose from.”
Roger rolled his eyes, but he moved
closer to one of the racks of dresses that surrounded them. For the middle of the week, he wasn’t all
that happy to see so many people in the store.
He wasn’t sure how happy they were to see him either. But he didn’t have much choice in the
matter. Jennifer had said he looked
silly. He knew without a doubt that he
looked just plain stupid! Well, he
guessed he better start getting used to doing this kind of shopping anyway. No doubt in the future he would be doing a
lot more of it. Summoning up his
courage, he did his best to ignore everyone else around him and started
rummaging through the dresses in front of him, trying to figure out if each
dress would be something decent that he could wear to church.
“What happened to that wig they put
on you when you got your makeover?”
Jennifer asked as she watched him shopping – finally.
“It’s at home,” Roger replied.
“You wore everything else, but you
left the wig home? You didn’t think it
might make you look more like a woman so at least some of these people here might
not stare at you so much?”
“I didn’t think about it,” Roger
replied. There was no way that he was
going to tell her that it was Carol who insisted that he dress as he did. And in fact, he never even considered wearing
the wig.
“Yet you wore makeup and everything
else,” Jennifer noted.
“Not everything,” Roger replied, a
bit sarcastically. “I didn’t wear my
dress.”
“Well you might have worn that too… as well as
the wig! Damn, Roger. I saw the before and after pictures from that
makeover you got. I was surprised that
whoever did it made you look that good!”
“Me too,” Roger agreed.
“Well if you could learn to do your
makeup like that, then if you just dressed a bit… more consistently anyway
instead of half man and half woman, don’t you think that at least some of the
people around you might ignore you instead of everyone thinking you’re the
center of attention?”
“I’m working on it,” Roger replied,
although his tone of voice was anything but happy.
Jennifer came up behind him and put
her hand on his shoulder, which earned him a rather uncomfortable frigid jolt
in the usual expected place. “Sorry,”
she said. “I know this has to be
embarrassing for you. And probably
somewhat difficult too.”
“You think?” Roger replied, still
not happy with the situation. “I’m sorry
too. This is all something I have to
learn to do. I just have no clue how to
go about any of it or what it is I need to be looking for. This is all so new to me and I haven’t
exactly had much help.”
“And I still can’t understand why
you’re doing it,” Jennifer said. “Like I
told you before, I never imagined you doing something like this.”
“Me either, I guess,” Roger
replied. “But I’m doing it.”
“I just don’t get the why’s of it?”
Roger just shook his head. “Don’t ask.
Please don’t ask.”
“I wish you wouldn’t keep saying
that! It doesn’t help!”
To change the subject, Roger pulled
one of the dresses out further. “What do
you think of this?”
Jennifer looked at it. “It’s as nice as any of the others. Are you sure you want that style?”
Roger looked carefully at the
dress. “What’s wrong with it?”
“Nothing at all. I just figured that since you really don’t
have that much of a figure… not counting your bigger breasts tonight, that you
might want to go with something with a belt instead. That would help give you more of a waistline
than what you’ve got now… which is none.”
“See, that’s why I need help. Little things like that are what I don’t
know.” Smiling, he put the dress back
and searched out ones with belts instead.
Ten minutes later, Roger carried
two different dresses into the changing room to try them on.
“Want some help?” Jennifer asked
before he entered.
Roger was about to say no, but he
thought of something first. “If I say
yes, will that mean that I won’t have to come out here to show you how they look?”
“Of course! I mean, you can stay in there and decide it
for yourself without coming out, but I’d really like to see them... on you!”
Roger had a lot of misgivings about
that. But one glance around showed him
several people who seemed to be looking at him.
He’d rather not let them see him coming out of there with a dress
on. So against his better judgment he
said, “Okay, I guess.”
Jennifer didn’t need any further
invitation.
Roger’s first problem to overcome
was the intense cold that invaded his groin the moment he even thought about
undressing in front of her. And since
the room was so small and she was so close, that made things even worse! Gritting his teeth, he did his best to ignore
the outright painful cold that still seemed to be growing.
“Are you okay?” Jennifer asked.
“You look like you’re in pain.”
“It’s nothing,” Roger replied.
“Sure?”
He nodded and began removing his
shirt. A minute later, his top was only
covered by the large size bra he had on.
“What’s in there?” Jennifer asked
before he could get any further. She
turned him around so she could see his bra cups better, and then she pulled one
out to peer inside. “Pantyhose!” she
exclaimed softly. “They don’t fill that
bra very well,” she noted. “There’s a
lot of empty space left over. You really
need something better to put in there.”
Roger couldn’t say anything yet,
because her touch was nearly killing him with frigid cold pain. No, there was certainly no danger of him
getting a hard-on with her tonight! “Like
what?” he finally managed to grunt out.
“Like better breast forms. You know, like the kind that women use if
they get a mastectomy. But you know what
you really need?”
“What,” Roger managed to get out of
his mouth where his jaw was practically locked in position.
“You need a different bra!”
There were a number of things Roger
thought of saying… or asking… but the shortest reply was the easiest to get out
of his mouth. “I do?”
Jennifer turned him around and
pulled out the back strap of his bra and checked the tag inside. “I thought so. That bra is way, way too big. I don’t know what warped kind of fantasies
you were thinking of when you bought it, but if you want to look somewhat
normal, I wouldn’t go trying to sport that kind of breasts all over the
place. And obviously those ‘A’ cup bras
you wear everywhere else are really too small for your size.”
“So?” Roger got out, easier than he
expected.
“So… for you… maybe you should
consider something more the size of a ‘C’ cup instead. That’s just my opinion though. It’s your figure that you’ll be showing off. But if you want to show overly large boobs,
then go for it!”
Roger blinked as he felt himself
starting to get a little more used to the pain in his very sensitive area.
“Will you help me find one?”
Jennifer smiled. “I’ll be happy to. Now let’s see that red dress on you
first. I think that should look really
nice on you!”
Nice? On him?
Roger had some serious doubts about that!
Janice raised her eyebrows as Carol
delightedly told her how she had dressed Roger for his shopping “date.” The words, “poor Roger” sprang to her mind,
yet she really felt no sympathy for him at all.
The fact that she was home but he hadn’t returned yet had her somewhat
concerned. “It sounds wonderful,
dear. I can’t wait to see him. I’m really only surprised that he hasn’t
returned yet.”
Carol’s face clouded a bit. “He’s been gone quite a while now. Maybe we should call him,” she suggested.
Janice nodded and headed for her
purse to grab her cell phone. But as she
did, she saw the lights from his truck turning into the driveway. “Here he is now,” she said, somewhat
relieved. Two minutes later, she held
the front door open so he could come in.
He had several large bags in his hands.
“Have a good trip?” she asked.
Roger wasn’t sure how to answer
that, so he held up the bags and replied, “At least I got more stuff.” For which he heard Carol giggle.
“I’d love to see what you bought,”
Janice said as she closed the front door again.
Roger had no doubt at all that she
would. Carol too for that matter!
“And how did things go with Miss
White today?” Janice asked as she studied the way Carol had dressed him. “Did she find the way you look… interesting?”
Roger rolled his eyes as he headed
for the couch in the living room. “She
thought I looked silly!” he stated. Then
he added, “But at the same time, I think she appreciated some of what I
wore. I think she just thought that if I
was going to dress as a woman, at least somewhat, to go out and buy women’s
clothes, then I should have gone a lot further with it so I wouldn’t have been
the center of attention for most of the other shoppers. She wasn’t too happy about that.” He looked over toward Carol. “Neither was I.” The only reaction from Carol for that was her
giggle. She would!
“All the more reason for you to
continue making progress on your journey toward becoming Candy,” Janice noted.
Roger purposely didn’t reply to
that. Instead, he took one of the bags
in his hands and opened it, and simply dumped the contents out on the couch. He picked up three white bras. “Jennifer suggested that I go with ‘C’ cup
bras instead of the small ones I usually wear… or the extra-large ones like
I’ve got on now. She thought I might
look more normal with the ‘C’ cup. So I
went ahead and got some. And we found
some of these breast forms to go in them,” he added as he set the bras in a
pile on the couch and then set the forms on top of them. He wasn’t sure how either Janice or Carol
would take that… since Carol had purposely gotten him the extra-large bras to
begin with.
“Sounds quite reasonable to me,”
Janice replied. “A woman of your age and
height would most likely have far bigger breasts than you normally show.”
“I like the really big ones on him,
Momma,” Carol said.
“Yes, I’m sure you do dear. And for special occasions I’m sure they will
undoubtedly be quite interesting. But
Mr. Brinkley is in the process of becoming as much of a woman as we can
possibly make him. We don’t want him to
become a mockery of women instead. That
would reflect badly on not only us, but all women.”
“I still like the bigger ones,”
Carol replied, only less determinedly.
Roger noticed Janice simply rolling
her eyes before turning back to the items on the couch. He picked up a simple cotton nightgown, but
he left it folded. “You said I could
wear one of these at night now,” he told her as he held up the still folded
gown.”
“Open it up,” Janice requested, “so
we can see it.”
Roger let the folds fall out of it
as he found the shoulders to hold it by.
It was a simple cotton nightgown with just a tiny flower print on the
material.
“Very nice,” Janice said. “And you may wear it tonight when you go to
sleep,” she confirmed.
Roger was glad. More so because it meant that he wouldn’t be
sleeping in the cage tonight! He turned
back to what was on the couch and opened another bag and pulled out several
items. Setting the pile on the couch, he
held up and displayed a short sleeved patterned pullover top and another
pullover top done in a bold multi-colored flower pattern. “I figured these would be good to wear around
the house here… and maybe allow me to eat at the table now,” he added.
“That of course depends on what
else you’re wearing along with them,” Janice replied.
For his answer, Roger grabbed and
held up a tan denim style skirt. “How
about with this?” he asked.
“That should go quite well with
those pretty tops,” Janice agreed.
“However, you’re still going to have to make an effort with your makeup…
and I think your wig will need to be included as well.”
Roger just nodded. He set the skirt down and picked up the last
thing he had pulled out of the bag. “I
wasn’t sure if you would let me go with any pants yet, but I got these just in
case,” he said as he held up a pair of women’s jeans with silver designs
stitched in the back pockets.
“Mr. Brinkley,” Janice replied,
“other than for church, how often have you seen Carol or myself wearing dresses
and skirts? Well, I admit that I tend to
wear them far more often than Carol does, especially comfortable ones around
the house. But either way, pants are
very much an acceptable form of dress for women, and I see nothing wrong with
you wearing them either.”
Roger felt much more relieved. He also made a mental note to get more
pants. A lot more pants!
“And how about something different
to wear to church?” Janice asked. “Did
you manage to find something for that as well?”
For that, Roger opened his final
bag and withdrew his new dress.
“Jennifer said she really liked this on me,” he said as he held the
thing up so they could see it better. It
was a dark red dress with black showing inside each of the pleats on the skirt. There was also a thin black belt encircling
the waist.”
“Very nice, Mr. Brinkley. Very nice indeed! I can’t wait to see you in it.” Her face clouded just a bit. “But I’m afraid that Carol and I won’t be
here to see you wear it to church this coming Sunday. You’re going to have to go without us.”
“Can’t I just skip going this
week?” Roger asked hopefully.
“Of course not, Mr. Brinkley! There is no reason at all why you can’t
attend without us being there! You even
have several new friends there now who I’m more than sure are looking forward
to seeing you there. No, you will have
to make the journey yourself. Carol and
I will simply have to wait until we get home that night before we can see how
you look in your new dress.”
Roger nodded. He wasn’t happy about that at all. But at least everyone in the church had been
very kind to him. And… he wouldn’t have
to worry about going to that stupid restaurant afterwards!
“Mr. Brinkley,” Janice said as he
was putting the clothes back in the bags.
“I will be keeping Carol home from school on Friday. I’m afraid that I’m going to need her with
me. We will be leaving here sometime
Friday morning and will most likely not return until Sunday evening
sometime. I expect that whenever you are
here in the house, you will endeavor to become Candy as much as you possibly
can. I expect you to continue to find
ways to improve yourself every single day.
There can be no let-up Mr. Brinkley… whether Carol or myself is here or
not. Is that understood?”
Roger just nodded sadly. Even without them there, he was still doomed
to becoming – Candy. A small thought
occurred to him. “Carol is going to miss
school on Friday. You know we have a
major test in that class next week.”
“Fear not, Mr. Brinkley. I will make sure that she stays on top of her
studies while we are gone.”
Roger just nodded. Actually, despite the fact that he had to continue
to be Candy as much as possible, he was very much looking forward to having
both Carol and Janice completely out of his life… if only for just a few days.
“Now,” said Janice. “There is just one other thing.”
“Yes?” Roger asked.
“Do you have a ladder I can borrow
for a few days?”
“A ladder?”
Stan checked the clock. Jennifer hadn’t called yet to tell him how
things went with the shopping trip she was supposed to take with Roger. Of course, she never said she would call. Were they back yet? He was tempted to call her to find out if she
was home. He knew he was fretting about
it more than he should, but he couldn’t help it. Was she home yet… alone? Or were she and Roger in bed together…
picking up the romance they once had and starting it up again?
Roger was still dressed exactly as
he had been while he was out shopping. He
was glad that Janice had readily agreed that he had done enough so that he
wouldn’t have to sleep in the cage. But
he barely gave that nightmare another thought.
He was staring at what he could see of himself in the makeup mirror that
was propped up on his dresser. He really
couldn’t see much of the clothes he was wearing at all, but he wasn’t worried
about seeing them. He was looking at
himself, but he wasn’t seeing the image reflected in the mirror. His mind was looking elsewhere.
His mind conjured up a picture of
himself as Roger, but the image was becoming more and more faded… while at the
same time, a still vague and foggy image of Candy was starting to superimpose
itself over top. But how much longer
would it be before that vague foggy image of Candy became much clearer… and the
image of Roger would be all too difficult to see?
