The Housekeeper - Chapter 32 Part 3 of 3

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?