The Housekeeper - Chapter 25

The Housekeeper

By Karen Singer

Chapter 25

Jacobs had a list of things he checked on every morning when he came into work, and one of those things that had been added to his list was checking on where Janice Stokley’s car was.  He wasn’t sure if he was surprised or not to see that it was still in Gainesville – unmoved.  Was something wrong with the car?  Was it being repaired or something?  Having no answers, he was forced to put it out of his mind and check on the next thing on his list.

Now that his cold was easing up some, Roger was starting to feel more like himself.  Mentally anyway.  He was still on all the cold medicine, but at least today the daytime version of the medicine didn’t seem to be clouding his head as much.  Today, he was much more able to appreciate standing up in front of the class and writing on the blackboard – without the damn bra causing him problems.

His biggest problem of the day wasn’t the students, and it wasn’t his cold.  His biggest problem was the fact that he couldn’t stop worrying about having to go shopping later… with Janice… for a dress that he could wear to church.  He was still having trouble wrapping his mind around that.  That was his biggest problem of the day, until… Jennifer White sat down in front of him during lunch. 

“You don’t have to look so disturbed to see me!” Jennifer stated as she saw the look on his face.

“Sorry,” Roger replied, but all he could think about just then was the frigid cold that was already starting to make itself known in the most sensitive part of his groin.

“Chicken soup again?” she asked as she leaned over the table to try to smell it better.

Roger nodded.  “Yeah,” he replied as he felt the cold still growing down below.  Did she have to wear her hair down like that?  It made him want to reach out and caress it… not to mention caressing the rest of her too.  How long had it been now since he’d had any sexual relief?

“Please can I try a little taste?” she asked.

He almost said yes, but he as he stared at the spoon in his hand he remembered, “I don’t think you want to… I have a cold, remember?”

Jennifer quickly dug into the large purse she had hung on the back of her chair and produced a spoon.  “Ta-daaa!” she sang as she held it up.

Roger gave in and handed over the thermos.

“Oh… this is good!” Jennifer exclaimed as she stuffed a spoonful of the hearty soup into her mouth.  She handed the thermos back to Roger.  “She really can cook!” she exclaimed.  “Do you think that maybe she would show me how she makes it sometime?”

Roger was doing his absolute best to not show any sign of distress as his now totally frozen cock lurched in pain.  It wasn’t that he didn’t want Jennifer to come see him, it was just that he liked her… an awful lot… and her coming to the house would not only be painful for him… physically, thanks to Janice’s little curse… but Janice Stokley was a nightmare!  He simply feared for Jennifer’s safety!  “Ummm… I don’t know,” he was finally forced to admit.  He watched as she started in on her own lunch that she had bought from the cafeteria.  As tired as he was starting to get of the chicken soup, it was miles better than what she was eating.

“So how’s your new business going?” Jennifer asked with her mouth full of food.

“Pretty good right now,” Roger replied.  “I got my first bit of profit last night.”

“Oh yeah?  What did you have to do for it?”

“Other than fix a broken window?  Put up with three hours’ worth of questions from an old lady who couldn’t seem to get tired of the show!”

Jennifer almost spit her food out of her mouth as she laughed.  “You’re kidding!”

“Not one bit!” Roger replied.

“What’s so funny?” Stan asked as he sat down with his own tray.

“Some old lady paid to watch Roger fixing a broken window last night,” Jennifer replied.

“She paid to watch?”

“Well, actually, she paid to have the window fixed,” Roger replied.  “But the only real reason I was there was so that she could see if I would actually show up and do it in those boots… and she kept asking me stupid questions the entire time I was there.  A job that should have taken me less than two hours easily stretched into three!”

“Huh,” Stan replied as he bit into the hamburger he had just bought.  “I’m not surprised.”

“So do you have any more jobs lined up?” Jennifer asked.

“I’m starting on a big one this weekend… rebuilding a deck.”

“Oh?  Where is it?” Jennifer asked.

“Down on the way to Gainesville,” Roger replied.

“If you give me some directions, I might show up,” Jennifer said.

Roger was shocked.  “Not… a good idea,” he replied.

“Why not?”

Roger had to think of a good reason.  “Because I’ll be doing nothing but deconstruction.  It could be dangerous.”  It wasn’t a good reason, but it was all he could think of.  The last thing he needed was to be putting on a show for his friends too… especially Jennifer White!

Jennifer looked briefly over toward Stan.  She had struck out.

“Need some help?” Stan asked.  “I may not be the best with a hammer, but I should be able to tear something apart well enough.”

Roger didn’t know if he was scared or shocked.  First Jennifer had wanted to stop by to see him working, and now Stan was asking if he could help.  “Um… I don’t know what I could pay you,” he replied.  “I didn’t figure the cost of extra labor into my job estimate.”

“Did I ask to get paid?  Look, I’m just trying to help out a friend, okay?  And face it, you haven’t exactly been yourself lately.  You look like you could use a little extra help.”

Roger shook his head.  “Please don’t!” he said as he grabbed his things and got to his feet.  “Don’t worry about me, okay?”  He quickly got out of there.  He didn’t want to involve any of his friends in any of his problems.  The situation was simply… too dangerous!

“Well, we tried,” Jennifer said as she watched Roger’s back disappear out the door. 

“Something is going on,” Stan stated.  “I’m even more convinced of it now than ever!”

“So what do we do?”

Stan shook his head.  “I don’t know yet.  But I’m open to ideas.”

Roger was shaking… especially inside.  He was sitting in the back seat of Janice’s car as they pulled into the parking lot of the store.  It was a store Roger had never been into before… one where he was certain that more women shopped than men. 

He was again wearing a bra with the socks stuffed into it under his clothes.  He was also wearing a pair of the pantyhose that Janice had told him to buy a few days ago.  And… he was again wearing the crazy high heeled shoes strapped to his feet.  And that of course didn’t even count the frilly yellow panties he had been wearing all day as well.  All of that was what he was wearing along with the clothes he had worn to work… minus the sports jacket and tie.  His fake breasts would be on display from the moment he got out of the car.  He supposed he should be glad that Janice hadn’t mentioned anything at all about makeup for his face.  He purposely didn’t bring that little subject up at all!

Janice parked the car, then turned back toward Roger.  “Mr. Brinkley,” she said, “I expect you to cooperate fully while we’re in there.  We are investing in your direct future this evening so it’s in your very best interest to not only cooperate, but to show as much interest as you can tonight.  Learn something here, Mr. Brinkley.  Take advantage of the opportunity while Carol and I are here to help you… because soon you’ll be on your own to do things like this without our help.  And Mr. Brinkley, I won’t hesitate to put you into a trance at the first sign that I see you not cooperating.  Do I make myself clear?”

Roger, shaking even more, nodded his head.  “Yes,” he replied.  He didn’t chance trying to even say another word. 

As they entered the store, Roger wanted to walk behind Janice and Carol.  He was hoping they would act as a shield so he wouldn’t be so much on display.  But Janice insisted on walking right next to him and Carol lagged behind… all too often stopping to look at something that she was more interested in.  Which left Roger feeling nothing but totally exposed from all angles.  He didn’t spot many men in the store, but most of the ones he did see were almost always in the company of women.  Their wives he figured.  Before he knew it, he was surrounded by a world of women’s clothes.  A world he knew nothing about.  But he was guessing that he was about to learn a lot about that world… and soon.  In fact, starting now.

He knew he had to be causing some raised eyebrows or some very curious looks, but what could he do about it?  He did his best to ignore everyone else and pay most of his attention to Janice.

“Now Mr. Brinkley,” Janice said, “Have you given any thought to what kind of dress you’d like to look for?”

“Not exactly,” Roger replied.  “I was having too much trouble all day just picturing myself buying any kind of dress… let alone wearing one to church.”

Janice smiled. “I fully understand,” she replied.  “But now I’m afraid it’s time to move past the point of worrying about it happening, and get on with things.  So, what kind of dress would you think would be most appropriate for you?”

“Appropriate?  Other than none, I don’t know.  I guess something very conservative.  I don’t think I’m ready to make much of a fashion statement yet.”

“Good point, Mr. Brinkley.  Something conservative would be a very good idea for church.  And as for the fashion statement… I have no doubt that we’ll get there in time, Mr. Brinkley.  No doubt at all.”

That was not something that Roger wanted to think about!  A few minutes later, he was standing next to Janice as she briefly looked through rack after rack of dresses… only spending a few glances at a few of them as she pulled them out for a better look. 

“Do you have any preferences as to style or color?” Janice asked.

“Something dark?” Roger replied questioningly.  “As I said, I don’t think I’m ready to make a fashion statement yet.”  What he didn’t say, was that he figured that something dark wouldn’t be quite as noticeable as something bright and colorful.

“It’s spring, Mr. Brinkley.  We’re not going to find a lot of dark clothing this time of year.  And I think you should start wrapping your head around the concept of wearing things that look pretty instead of muted and uninteresting.  You’re becoming a woman Mr. Brinkley.  Get used to that idea.”

Get used to it?  How?  But Roger held his tongue and said nothing. 

Janice moved on to another rack of dresses and started looking more closely at them as she slid the hangers around on the rack.  “Now see, these are all lovely.  Any one of them would be very appropriate to wear to church.  What do you think?”

What did he think?  What did he know about any such thing?  “I guess they’re okay,” was all he could reply.

“Why don’t you pick several out and try them on,” Janice suggested.

Roger’s panic increased by a lot.  It wasn’t just that he would have to try some on, but now she wanted him to pick something out by himself!  He started to slowly look at a few of the dresses.  “Um… what size should I be looking at?”

“A very good question,” Janice replied.  “I think we’ll start with the size sixteens.  You’re a bit big in the shoulders and arms… not to mention the rest of your body… so we’ll start there and see if we have to move up a size or two.”

Not really knowing what he was doing, Roger pulled one off the rack in an orange and white print pattern where the material didn’t seem quite as flimsy or thin as some of the other dresses seemed to be.  The neckline was mostly square except for a small cutout in the center that didn’t plunge down too far, which he figured was a good thing.  It had short sleeves, which wouldn’t hide his arms at all, but then all the dresses in front of him seemed to have short sleeves… or no sleeves at all.  The skirt of the dress appeared to be somewhat full… and didn’t look to be too short.  He examined it, then held it up for Janice to see.

“It’s certainly a good selection,” she said.  “Why not choose a few to try on.  They’re all going to fit differently.”

Roger was looking for ways to get this over with fast, not prolong the agony.  But after draping the one dress over his arm… which made him feel funny inside, he continued to look through the dresses in front of him.

“There are other racks as well for you to choose from,” Janice told him. 

But instead of looking anywhere else, he pulled another dress off the rack.  This one was black with white polka dots that seemed sparse on top, but continually grew more and more numerous as the pattern continued down toward the hem of the dress.  This one had a rounded neckline and just small cap sleeves that would probably just barely cover his shoulders.  It also had a very thin but prominent red belt encircling the waist.  But it was also mostly dark in color instead of something more colorful.  He held it up for Janice to see.

“You like that one as well?  Excellent.  Any others?”

“Can I just start with these and see how they fit?”

Janice nodded.  “It might be a good idea.  That way we can see if we’re looking at the right sizes or not.” 

A few minutes later he was in one of the dressing rooms while Janice and Carol were standing waiting for him to change his clothes and show them the dresses – on him!  He removed his pants and shirt and slipped the orange and white dress on first.  It was more fitted in the waist than he expected.  But then he was faced with trying to zip the thing up in the back.  He tried several different ways, but couldn’t manage to get the darn zipper up more than a few inches – only because he couldn’t reach the darn thing.  Cursing women’s clothes in general and praying that there were no other customers around, he shyly stepped out of the changing room.  Fortunately, the only people he saw in the limited area were Janice and Carol.  Whew!

“Ah… Mr. Brinkley,” Janice said in a very pleased voice as she heard a slight giggle out of her daughter.  “That didn’t take you too long at all.”

“Only because I can’t reach the darn zipper on this thing,” he replied.  “Maybe I’d do better with something that wouldn’t be so hard to fasten.”

“Nonsense!  You need to get used to all these different types of clothes.  And I’m afraid that dresses that zip up the back may be bothersome, for all of us, but they’re also all too common.  So it’s probably a good thing that you get the chance to learn and get used to them.  Here, turn around and I’ll help you.”

Roger turned his back to her, where he didn’t have to see the all too delighted smile on Carol’s face… that he’d love nothing more than to wipe off of her – permanently!  He felt Janice grab the zipper and tug.  Slowly, the dress became much tighter around his chest as she continued to move the zipper upwards.  Then all of a sudden it seemed to go much easier and faster, and she finished pulling the zipper completely into place. 

“There,” she said, sounding somewhat satisfied.  “Now turn around so we can see better.”

Roger turned around again, feeling more foolish than ever.  He was very aware of how tight and clingy the dress felt against his entire body… well, his upper body anyway.  Since the dress had a fairly full skirt, he couldn’t feel much of anything of it below the high waistline the dress seemed to have.  “Too tight?” he asked… or suggested.

Janice looked closely at the fit to consider that point.  “I don’t think so at all.  It’s a very fitted style that’s designed to hug your body.  I think that’s all you’re noticing.  If anything, it almost looks too big in some places, particularly the length.  But then in areas, like your upper chest and shoulders, it doesn’t really look big at all.  How does it feel?”

“Weird!”  For which he heard Carol laugh.  And he couldn’t blame her one bit for that!

“I have no doubt at all that it feels that way to you,” Janice replied.  “But give it time and I’m sure you’ll get quite comfortable with it.  Now, how about the other dress?  Let’s see that one on you as well.”

After letting Janice pull the zipper down for him, he went back into the changing room to try on the black dress.  This one also zipped up the back, but he could tell immediately that this dress also felt different on him.  The material was a little heaver… yet softer.  And the skirt wasn’t nearly as full as the other dress, so he was more aware of how the entire dress caressed his body… more so than the other dress had.  He wasn’t sure if that was good or bad.  And he hadn’t even zipped up the zipper in the back yet!  Once again, he cautiously stepped out of the changing room to show Janice.

“My, Mr. Brinkley,” Janice declared, “that dress looks somewhat good on you already.  Here turn around and let me zip you up.”

Roger turned his back to her, and a moment later felt all too much of the dress encasing his body – all over!  He turned back to her so she could see.  This time he was much more aware of the narrower skirt around his hips and legs.

“Yes, that one is lovely on you.  I’m afraid it shows off how unfeminine your shoulders are, but at the same time, it… somewhat… gives you a better figure.  Like the other one, it looks a bit too long as well.  I’m sure that’s because the size is a bit too big for your height, but that’s something that can’t be helped yet.  Still, it’s a lovely dress and it should suit you perfectly for church.”

Roger didn’t want to be reminded of wearing a dress to church again, but he supposed that if he had to, he’d rather wear one that looked better on him than one that didn’t.  “So can I just get this one?” he asked.

“If that’s all you want to buy tonight,” Janice replied.  “But you’re more than welcome to continue shopping.  You’re going to need many more things in the future, Mr. Brinkley.”

Roger was aware of that, but he really just wanted to get out of there.  “I’m aware of that,” he replied.  “But right now, I’m still having problems… adjusting.”

“Very well, Mr. Brinkley.  If you just want to get that one dress tonight, that’s fine.  But may I also suggest you get yourself a slip to wear under it… and a purse to carry your things in would certainly be a very good idea as well.”

Roger stared at her for a moment as his head wrapped itself around those concepts.  “Where do I find them?” he asked.

“Right this way, Mr. Brinkley,” Janice said with a small smile as she turned and headed toward another section of the women’s wear department.

It didn’t take them long to find the right size and type of slip for him to wear under “his” dress, but it did take a long time to pick out a pocketbook for him to carry… only because Janice refused to help him in the endeavor.  “You have to learn to do these things for yourself, Mr. Brinkley,” she told him.  Which left Roger faced with a seemingly endless display of purses in all types, sizes, colors, and configurations.  He had no choice but to try to go about selecting something – logically.  And he was more than aware that he would soon probably be carrying the thing to more than just church!

Realizing this, he took the time to open more than a few and examine not only the way they were configured – inside and out, but also how the darn things opened in the first place.  He figured he wanted something that would be secure – so not only things wouldn’t fall out of it… or thieves could easily steal things out of it… but he still needed to get into it easily himself.  He finally settled on one in black leather with a large flap that came over the main inside pocket and fastened down near the bottom of the front.  It had several pockets both inside and outside... and most importantly, it didn’t appear to be too eye-catching! 

Fifteen minutes later, he walked out of the store with a new dress, a new purse, and a slip to go under the dress.  And the reality of having to wear it all to church on Sunday was starting to sink in.  And he was still trying to picture himself doing it… but it was something he still couldn’t really picture yet at all!

That night, in order to sleep outside of the cage, Roger had to put his dress on over and over again… and remove it over and over again… each time trying to get the zipper on the back of the dress up or down – by himself.  It wasn’t long before it was all he could do to not rip the dress to shreds – in totally anger and frustration!

“What are we going to do about Roger?” Jennifer asked.

Stan’s rolled his eyes.  Thinking about Roger was the last thing he wanted to do right now.  They had just made love.  She was still cuddled against his body, her head was resting on his shoulder.  How the hell could she possibly think about Roger at a time like this?  It didn’t exactly make him feel very good!  “I don’t know,” he finally replied.  “But I can tell you this, he’s definitely not himself lately.”

“You can say that again!” Jennifer replied.  “He looks like hell!”

“Yeah, he does,” Stan agreed.  “But it’s more than that.  I mean, he’s usually the most money conscious guy you could possibly imagine.  Cheap in fact!”

“Yeah, but he spent most of his money on that house.  And I happen to know that he’s got almost nothing left of the little inheritance he got from his father.  It’s all gone into rebuilding his house.  But you have to admit, he’s doing a real nice job with it.”

“Yeah, real nice!  But now, all of a sudden, he’s hired a housekeeper?  That’s weird enough to begin with!  And I know you had to see that Cadillac he drove to school in.  And now he’s finally traded that old beater of a car he was driving around in for a new truck?  Well, he needed the truck.  I don’t see why he ever bought that piece of junk he had before in the first place.  But the point is… did he win some kind of lottery?  I just don’t see it.  Mister – all too careful with his money – is suddenly spending it like it’s going out of style.  And he’s quitting teaching as well!”

“Yeah,” Jennifer agreed.  “So… what’s going on?”

“I don’t know,” Stan replied.  “But something’s not right!”