The Housekeeper - Chapter 23

The Housekeeper

By Karen Singer

Chapter 23

The intense cold that invaded his private region didn’t hit all at once, but it grew rapidly as his eyes took in the long flowing blond hair, the beautiful features of the pale skinned face, and the deep blue eyes of Jennifer White as she sat down across from him at the table in the teacher’s lounge.  His breath caught at just the sight of her.  And then he turned his head quickly to the side as he sneezed violently.  After wiping his nose with a tissue he had pulled from his pocket, he turned his head back to her again.  The excited impish expression that had been on her face was now replaced by one of concern.

“You have a cold!” she exclaimed somewhat horrified.

Roger finished wiping his nose.  “Yeah,” he agreed.  “A bad one.”

Jennifer caught a whiff of the soup in the thermos that Roger was eating from.  “That smells good!  Chicken soup?”

Roger nodded.  “Yeah.”  He was totally undecided though as to whether or not he wanted Jennifer to leave.  On the one hand, he was still terribly hung up over her… but on the other hand, the reaction he got because he was so hung up over her was currently causing his cock to feel like it had been dipped in dry ice!  And that was despite him having a terrible cold.

“What kind?” Jennifer asked. 

“Homemade.”

“Wow!  I heard you had a housekeeper now.  And Stan told me you said she was a great cook.”

Roger nodded as he spooned some more of the soup from the thermos and stuck it into his mouth – mostly because by doing that he wouldn’t have to look at her… pretty face.  “Yeah,” he said into his thermos, “That’s one thing I really like about her.”  He didn’t bother to mention that it was the only thing he liked about her… and that he’d gladly trade that for some way to just get rid of her – permanently!

Jennifer leaned closer, the excited impish grin back on her face.  “So tell me,” she said, “Is it true… what you’re doing with the women’s boots?”

Roger was forced to look up at her.  “Who told you about that?”

“Stan.”

Roger nodded and went back to his soup.  “I should have guessed.  He’s really the only one who knows… other than a couple of new clients I have already.”

“You mean… it’s working?  Already?  People are calling you to fix stuff just because of the boots?”

“Seems to be,” Roger replied as he spooned more of the soup out of his thermos.  Why couldn’t the hot soup thaw out his totally frozen cock?  Maybe he should just dump the whole thing in his lap!  Unfortunately, he knew perfectly well that it wouldn’t work.  But that didn’t mean he wasn’t tempted to try it.  He was starting to really wish that Jennifer hadn’t sat down in front of him.

“Can I see?” she asked.

He looked up at her, surprised at her question… and totally captivated by her beautiful flowing hair that framed her even more beautiful face… that instantly made his cock hurt even more.  “What do you mean?”

“I want to see them sometime… I mean… you wearing them!”

Roger shook his head.  “Please don’t,” he replied.  “It’s embarrassing enough.”

“So why are you doing it?  That’s what I don’t get.  You have to admit, I know you pretty darn well Roger, and I just can’t seem to even imagine you doing anything remotely like this.”

Roger stopped eating his soup and chanced gazing into her face again.  His cock was so painfully frozen now that it couldn’t get any worse.  He gazed at her, because he didn’t know how to answer.  Finally he looked back down into his thermos again.  “Believe it,” was all he said.

“Why?  It’s not you!”

“I guess it is,” he replied.  “Or it soon will be.”

Jennifer shook her head.  “I just don’t get it.”

Roger ignored her comment and went back to his hot soup.  If only his ice-cold cock could feel just a little bit of the warmth coming from the soup.  It would feel so much better.  As it was, he was afraid that if he stood up too fast, the darn thing might crack and fall off!

“So can I see sometime?” she asked again.

Roger was forced to look back at her again.  “You want to see me wearing the boots?”

Jennifer giggled a bit.  “Yeah!”

Roger shook his head.  How could he get out of this?  “Let’s wait a while first,” he replied.  “I don’t think I’m ready for close friends to see it yet.”

“You let Stan see,” she replied.

“Give me some time,” he replied.  “Please!”

Jennifer looked at him seriously.  “Is it because you’re still mad that I dumped you?”

It was a moment before Roger could answer.  “Maybe,” he replied.  Actually, he didn’t really know what the answer should be.

“I had my reasons,” she said.

“What did I do wrong?” he chanced asking.

“Nothing.  It’s not you at all.  In fact, I really like you Roger.  It’s just… me!”

“That doesn’t tell me much,” Roger replied as he went back to his soup.

“Sorry,” she said.  “You’ll just have to take it for what it is.”

Instead of answering, he quickly turned his head to the side and sneezed again. 

“You really do look pretty miserable,” Jennifer noted with concern.  “And the fact that it looks like you haven’t had a haircut in several months isn’t helping the way you look either.  And now you’re quitting teaching… something I know you loved doing!  I just don’t get what’s up with you lately!”

“Nothing is up!” Roger replied testily.  And then he sneezed again.  “Damn cold!”

Jennifer White wasn’t all that sure about things.  She hadn’t really believed it when Stan had told her about what Roger was doing with the women’s boots.  It didn’t make sense at all… something that Stan was totally in agreement about.  Yet it seemed that Roger was going to do it.  And yet… he was also without a doubt very embarrassed by it.  So… why was he doing it?  No, things simply didn’t add up!  As soon as she got a chance, she decided she would have another little chat with Stan.  Maybe between the two of them they could figure out what was going on with Roger.

Roger quickly plucked a tissue from his pocket and sneezed into it again… then went back to writing on the board.

“Mr. Brinkley,” one of his brighter students called.  “Shouldn’t that be forty-two instead of thirty-six?”

Roger looked at what the student was talking about.  He had to study the problem for a minute before he realized that the student was correct… and he was wrong.  With a smile, he looked at him and said, “You’re exactly right!”  This was the second time… in this period alone that he had made an error like that.  His cold was affecting him worse than he thought!  “Tell you what,” he said to the class, “it seems my cold… or maybe the cold medicine I’m taking, is clearly messing with my head.  Why don’t you all just study for the rest of the period and hopefully tomorrow I’ll be doing at least a little better.”  His students needed no further encouragement.

Roger sat back down at his desk and blew his nose again into a fresh tissue.  Darn cold medicine.  And it was the daytime version of the stuff he had taken last night so it wasn’t supposed to cloud his brain or make him sleepy.  Well, he wasn’t exactly that sleepy, but his brain was sure foggy!  He had been making stupid mistakes like that all day!  The only bit of comfort he really had today was that he wasn’t wearing a stupid bra under his clothes.  Hooray!  He was sick of dealing with errant bra straps!

But now that his brain was a bit more idle, it again brought up a vision of Jennifer White sitting across from him while he had been eating.  And he again felt the cold starting to invade where he didn’t want it to invade.  He wasn’t all that happy that Stan had told her about the boots, but he wasn’t surprised by it either.  Since she had broken up with him, he had heard that she was going out with lots of different people… and Stan was a likely candidate.  He was simply jealous of Stan, that’s all… and all the other guys she went out with too!  He had gone out with Jennifer for several months before she had broken it off.  And he still didn’t exactly know why.

And now he was sitting here thinking about her again… which only made his stupid cock start to feel like it was freezing again.  Damn the curse that Janice Stokley had put on him!  Because that was how he thought of it now – as a curse!  A damn curse!

She had surprised him a bit this morning by telling him to take the new car to work instead of his old car.  Was that because she felt bad for making him sick?  Somehow, he doubted it.  One minute the darn woman could be the nicest person on earth… but then the next…  She was simply a nightmare!

He realized that after thinking about Janice for a few moments, his cock no longer felt frozen at all.  Hooray!  A cure!

Foremost on Janice’s list of things to accomplish, was finding Roger a new truck.  Or in this case, a used truck that didn’t cost too much.  And that was the biggest problem she was facing right now.  His latest paycheck was now in the bank, but his new business hadn’t brought in any money at all yet.  There was the money he should be getting from the Whittakers, one third of his estimate for the job that he would be doing for them, but he hadn’t gotten that money yet.  And the other job to fix the window was one he hadn’t done anything with yet either.  She was going to have to juggle his bills around a bit to make it all work.  Of course, she would also be “loaning” him some money to get things started, but she expected to later take that money back once things got rolling with his new business.  But in the meantime, she was going to have to be careful. 

She stared down at the list in front of her.  The top of the page specified a few models of trucks he was interested in.  Four by four was prominently spelled out on the list and underlined.  He had insisted that he needed that here in north Georgia, and she knew without a doubt that he was right.  Many of the places he could be working at would be on steep mountain roads… and many of the driveways in this part of the world required four wheel drive no matter what time of the year it was.  But winter was the worst to deal with by far.

She had mentally added another item to Roger’s list of requirements for the vehicle – a large car dealer.  Once they traded Roger’s old car for the truck they would buy, a large car dealer would be more likely to ship Roger’s old car off to an auction house somewhere instead of putting it on the lot to sell right there.  And she wanted the little bug attached to the car’s gas tank to go to the auction house as well.  Hopefully somewhere very far away!

She picked up the phone and called yet another car dealer that seemed to meet her requirements.  “Hello,” she said to the receptionist on the phone.  “I’d like to speak with a saleswoman please.  Someone who knows something about used pickup trucks.  And if you don’t have a woman I can speak with about it, please just tell me now so I can call somewhere else.”

After school… and also after Roger “had” to change clothes so he could again wear a bra with the socks stuffed into it along with his new boots, they all piled into Roger’s old car and drove it down the highway toward a car dealer in Gainesville, Georgia.  Roger was very torn over the trip.  He wasn’t looking forward to “proudly” displaying his new boots or his little breasts either… not to mention the fact that his cold still had him feeling pretty miserable.  Fortunately, the jacket he was wearing somewhat hid his breasts, but it did nothing to hide the heels on his boots that would be constantly on display.  But despite all that, he couldn’t help but look forward to trading in the battered little car that he was driving now for a new truck.  Well, a used truck of course.  But it would be a truck!

When they got there, they were quickly approached by one of the salesmen, and once again Janice asked for the saleswoman she had talked with on the phone earlier.  Roger wasn’t the least bit surprised by that.  The only problem this time, was that this time it was Roger who was really looking for a vehicle and not Janice.  And consequently, Janice pretty much stayed out of everything so that the saleswoman paid all her attention to Roger.  And Roger couldn’t help but notice how often she looked down at the boots that he was wearing.  He also noticed her looking more than a few times at his chest where the “bumps” were still just barely noticeable under his jacket.  He just hoped there was some way he could avoid removing his jacket so she wouldn’t get a better view of his “pert” little breasts.  Fortunately, the woman didn’t say one word to him about either his breasts or his boots. 

Roger wasn’t too sure about the money situation at all, but two hours later he had signed the paperwork for a loan to buy a five-year-old, dark blue, Dodge pickup truck.  The truck seemed to be in great condition.  It even had a good set of tires on it so he wouldn’t have to worry about that problem too soon.  And the extended cab, while small, also provided him with a place to keep some tools… not to mention a place for Carol to sit on the way home.  He didn’t care that Carol would be sitting in a “cramped” space one little bit!  In fact, as far as he was concerned, it wasn’t nearly “cramped” enough! 

Once the deal was finally done, Roger, Janice, and Carol all climbed into the new pickup truck and Roger was allowed to drive it home.  It felt good to him to be driving a truck again.  It made him feel more like a man… a real man!  Okay, so he was wearing women’s high heeled boots, panties, and a bra with balled up socks in it to give him the illusion of breasts, but it still made him feel more… masculine!

Roger’s good feeling of masculinity ended that night when Janice proclaimed that he once again had to sleep naked… and in the dog cage.  He hated Janice forcing him to crawl into the hated thing.  He hated everything about the cage.  It was difficult to turn around in the cage, but he did… and he wasn’t happy in the least to see Janice taking the lock that had so often been attached to the chain that had once held him captive in his bathroom… and putting it through the lock on the cage so there was no way he could possibly get out of the darn thing.  Captive!  He looked up at her with a pleading face… but there was no mercy there at all. And when the light was turned out and his bedroom door was closed, he could barely see anything at all. 

He rattled the cage a bit.  Pushing at it in various places, trying vainly to see if he could break out of it.  But he wasn’t nearly strong enough.  The cage designed to hold a very large breed of dog, was just as capable of holding him as well.  He sneezed again.  He didn’t even have any tissues to wipe his runny nose with.  Hopefully, the nighttime cold medicine would kick in soon and would put him mercifully asleep.  He curled up in the dog bed that lined the bottom of the cage and did his best to go to sleep.  Fortunately, the cold medicine did its job well. 

But his final thoughts of the night were centered around only one thing – how could he avoid sleeping in the cage in the future?  He knew the answer to that one.  But it involved doing things he’d rather not have to do.  But then, he already knew that he would have no choice in the matter at all.  Turning himself into a woman was already a foregone conclusion.

His medicine drugged mind woke in the early hours of the morning, he tried vainly to stretch out… but that privilege was denied him by the bars of the cage that confined him.  He tried again and again to push at the bars of his cage… only to be denied what he wanted so desperately to do – to stretch out full length and be comfortable.  His frustration over the matter grew and grew… and so did his hatred toward Janice.  But there was nothing he could do about either situation. 

Horribly frustrated and miserable, he tried to curl up into yet another position where he could go back to sleep.  As his brain tried to reach once again for that little bit of peace that sleep would bring, he remembered once again the many ways he had been forced to sleep since Carol and Janice had come into his life.  He had been chained and tied into the most torturous positions possible… and been forced to sleep that way.  And now, in the cage, where there was nothing holding his limbs to anything at all, the tight confines of the cage seemed almost worse to him that many of the other miserable things he had already endured.  Almost as if the cage had triggered a claustrophobia in him of some sort.  It was simply maddening. 

Sleep finally came again, but it was a very restless and uncomfortable sleep.  And when full morning finally arrived, and Janice herself came into the room to unlock and open his cage, he crawled out of it as fast as he could.  He looked up at her with a pleading expression on his face… and sneezed.  “What do I have to do to not sleep in that thing anymore?” he asked desperately.

Janice looked down at him.  “You know what you have to do, and I’ll be glad to lend whatever assistance I can to help you with it.  But you’re going to have to put forth the effort and actually do something.  Otherwise, I can assure you, that a few days from now, every time you have to use the bathroom, you’ll be going outside to do it like a dog instead.”  She continued to stare down at him… and the expression on his face never changed.  He simply continued to stare up at her… until he sneezed again.  “Come along,” she said, “It’s time for another dose of your medicine.”

Agent Ted Jacobs went into work and as he had done the day before, he checked the logs of where Janice Stokley’s car had been as well as where it was right then.  He noticed that it was currently in Gainesville instead of at their home.  Well, he knew that most people from all over that area did much of their shopping in the big city.  Evidently Janice was no exception.  He put it out of his mind and went to work on more immediate matters.

Roger’s tortured brain functioned somewhat better in school that day.  His cold was slightly better as well.  But both were far from perfect.  Both Jennifer and Stan sat with him while he ate another thermos of chicken soup during lunch… and both of them mentioned him wearing the women’s boots for his jobs again.  And he had to admit one more time that he was indeed planning on doing it.  But he didn’t mention anything else that was, or would soon, be happening.  One nightmare was bad enough.  No use making matters worse.

Once school was over, Roger drove Carol home where he changed clothes… unfortunately adding a bra with the balled up socks in it and his women’s boots to the work clothes he put on.  He spent a few minutes speaking with Janice before getting into his new truck and travelling up to the Whittakers house to pick up the down payment for the job he had to do for them.  He told them that most likely he would be able to start demolishing their old deck on Saturday.  He also warned them about the large dumpster he was going to order to hold all the debris. 

From there he travelled to the Adkins’ home where he was supposed to fix the broken window.  Fortunately, their home wasn’t far from where the Whittakers lived.  Rebecca Adkins turned out to be a very tiny and somewhat frail old woman.  Her husband looked to be in even worse shape.  But Roger noticed that they both stood there and watched him intently the entire time he thoroughly checked out what needed to be done with their window.  He was mostly sure that they spent a lot of time staring at the boots he was wearing.  He didn’t dare remove the loose jacket he was wearing and expose what his chest looked like.  No use adding more fuel to that fire!

The window had a single cracked pane.  One simple piece of glass that was still in place but really should be replaced.  The cracks in the pane though had been sealed with some kind of clear plastic tape – what looked like years ago.  And then he noticed a further problem with the window.  It had been painted shut, most likely multiple times.  Plus, the window was in an out of the way location where he was sure nobody ever used the thing.  He realized then that the only reason he was really there was so that Rebecca Adkins could see if he was indeed wearing women’s high heeled boots to work in like Elaine Whittaker had probably told her.  For that one reason alone, he decided to raise his rates for the job.

“I can fix the window pane fairly easily,” he told them.  “But since the window is painted shut and won’t open, do you want that fixed as well?”

Roger saw her husband starting to shake his head and say no, but his wife was just a little quicker.  “Yes, please, Mr. Brinkley.  We would like that very much.”

Roger nodded.  In other words, she wanted a chance to watch him longer.  He was definitely going to charge extra for this job!  He surveyed the window more carefully before figuring about what it would take him to do all the work, and then quoted them a price that was half again what he would have charged them.  Rebecca Adkins didn’t even blink an eye.  She accepted it on the spot.  Roger promised to be thrr tomorrow after school to fix their window.  He warned them that it would probably take him about three hours to repair and repaint part of the window frame.  He was fairly sure he could do it in less time, but he was going to make sure that they got charged for plenty of his time!

On the way home, as per Janice’s suggestion, he stopped at a store where he bought several pairs of pantyhose, and then spent a very embarrassing ten minutes in the makeup aisle picking out stuff that he wasn’t totally sure what it was… or did.  All he knew for sure about it was that it was makeup… various items that he hoped would probably be the basics of what he would need… and would enable him to sleep outside of his cage later that night.

When he got home, he turned the check from the Whittakers over to Janice, and then spent a very embarrassing hour going back and forth between the bathroom and the living room as he tried to work with the various makeup items he had bought.  He tried to apply the makeup… then each time he had to go out to show Janice and Carol how he looked. 

He felt like a child!  Like a little girl playing with her mother’s makeup.  He had no earthly idea how to use any of it at all.  And the only suggestions that Janice or Carol were giving him didn’t help a whole lot.  He got the impression that they were just enjoying laughing at him too much to give him any real help.  But his efforts though were rewarded when Janice did allow him to sleep outside the cage… and without anything binding him in any way. 

Freedom!  Sort of.