The Housekeeper - Chapter 32 Part 2 of 3

The Housekeeper

By Karen Singer

Chapter 32 Part 2 of 3

Joseph Halifax pulled his red Corvette into his driveway and drove quickly and carelessly around to the back of his building.  He pushed the button in his car to open his garage door and slowly started to pull in before the door was even fully open.  He turned off his engine and pushed the same button again to close the garage door after him.  Getting out of his car, he walked the few steps to the elevator.  He was happy to see that it was already on the ground floor so he didn’t have to wait for it.  Entering it, he closed the elevator door and pushed the button to take him up to the top floor where his apartment was.  He never noticed the door to the stairway at the other end of the garage closing.  He had never even thought to look in that direction.

Janice raced up the stairs.  She was panting by the time she got to Halifax’s floor.  She didn’t have time to stop to catch her breath, but very slowly and carefully, she opened the door leading out to the hallway on that floor.  Carefully poking her head partially out, she was just in time to see Halifax starting to punch in his security code before opening his door and disappearing. 

This wasn’t going to work.  She needed more time.  She needed a better way.  Fortunately, she had a pretty good idea of just what she would need to do.  Quietly, she headed back down the stairs to head back home again.  Such a long trip for such a tiny amount of information.  But it was necessary.  And she would be doing it again tomorrow.  But as her mind replayed over and over again what had occurred during her little experiment, she realized that maybe she wouldn’t need to come back tomorrow at all.  Her “plan” just needed a little more… refinement.

Carol’s head never moved, but her eyes did.  She sat at the kitchen table and watched as Roger put one of the dishes her mother had prepared earlier for their dinner, into the microwave.  Her mother was gone on business again.  She had a vague idea of what that business was, but of course, she knew no details at all. The only thing that kept this trip of her mother’s foremost on her mind, was something that her mother had told her earlier this morning – that she would need her help with something later in the week.  Her mother had never asked for her help in these matters before.  And now she was looking forward to it.

She studied the way Roger was dressed… the stupid fake breasts were fairly easy to spot under his dress shirt, but they weren’t nearly as noticeable as she would have liked… noticeable enough to embarrass him far more than she knew he already was.  She was still a bit upset over the fact that her mother had told her that Roger would be allowed to go shopping without her.  And that he would be going with Miss White.  She desperately wanted to see that.  But her mother had said…

The bell on the microwave dinged, and she watched as Roger pulled her dinner out for her.  She watched as he set the dinner on the table in front of her.  “You know where you have to eat!” she said, still never taking her eyes off of him.  And she watched as he sighed disappointedly, and dumped his dinner into his dog dish… and carried it to his corner… and bent down to eat it – like the dog he really was!  The sight brought a cruel smile to her face.

Carol picked up her fork and began eating, but still her eyes stayed on him.  His breasts weren’t as noticeable under that shirt as she thought they should be.  Her mother wasn’t letting her go along on the shopping trip with him like she wanted to.  And she was totally in charge of him otherwise.  Her mind churning, her eyes never once leaving him, she started eating.

As usual, she saw him finish eating before she did.  He ate amazingly fast all the time – even without the aid of any utensils.  Much like a real dog would eat she supposed.  She saw him get to his feet.  She saw him pour himself a cup of coffee.  And she saw him start to walk out of the kitchen with it as he usually did. 

“Wait a minute!”

Roger turned.

“I want you to wear something else,” Carol told him.

Warily, Roger asked, “What?”

Leaving what was left of her dinner, Carol led the way back toward his room.  “Get those clothes off,” she ordered without even looking back at him.

The fear in Roger’s stomach grew immensely… and it prevented him from pulling his clothes off right away.

“I said get undressed… now!” Carol said much more forcefully.  “Momma put me in charge!  You have to do whatever I tell you to!  Now get those clothes off!”

Roger’s mental conditioning forced him to start removing his clothes quickly.  That same mental conditioning told him he had no choice but to do whatever Carol wanted him to do.  He had to do whatever Janice ordered.  And she had made sure to include Carol in that mind warping conditioning as well.  He… had… no… choice.  And Carol… was downright cruel!

“Take that bra off as well,” Carol instructed as she opened his dresser and started searching the top drawer.  She found what she was looking for at the very back, and at the very bottom of all of his bras.  She pulled one out.  Perfect!  “Here, put this one on instead.”

Roger took the bra, although he’d much rather not.  It wasn’t one of the small ones he always wore now, it was one of the very large size that Carol had bought for him while Janice was still in prison.  Reluctantly, he fastened the thing around his chest.

Carol looked him over.  He was naked except for the pink and white panties he was wearing and the bra she had just given him.  She would have liked to overstuff that bra to immense proportions, but something told her that wouldn’t be a good idea this time.  The last time she had made him wear one of the extra-large bras, she had stuffed some of his shirts into it to overly fill it.  This time she needed something much… smaller!  But the usual sock balls he used with his smaller bras every day weren’t going to be big enough.  Searching his dresser, he pulled out two pairs of pantyhose from his drawer.  Since they weren’t rolled overly tight, they would work better than the socks he usually used.  They weren’t as big as she would like… not even as big as they needed to be, but it was all she could come up with at the time.

Unhappily, Roger stuffed a rolled up pair of pantyhose into each of the cups of his bra.  At least it was better than some of the things he had been forced to wear there.  Unfortunately, as soon as he had finished with that, Carol was handing him another pair of pantyhose!  “Put these on too!” Carol told him.  Ugh!

Thirty minutes later, Carol checked him over carefully and smiled.  The light blue short sleeved pullover shirt she had pulled out of his closet stretched tightly over his larger breasts.  You couldn’t miss them now.  His pants hid the pantyhose he was wearing… until you got down to his feet that were now encased in his very high heeled shoes.  She had made him put on just a tiny bit of makeup… not like he usually wore, but enough that if you looked at him, you could tell he was wearing it.  She had seriously considered making him wear his wig, but decided against it because there was too much of a chance that someone might actually mistake him for a woman.  But to finish his “look,” she had handed him his purse and made him put everything from his pockets into it.  “Okay, now you’re ready,” she said.  “Have fun tonight,” she added with an overly delighted smile.

Roger simply wanted to die.  He no longer wanted to walk out the door at all let alone go shopping… let alone go shopping with Jennifer.  He was desperately trying to find some way to argue… or at least get out of something, but the darn brain-washing Janice had warped his mind with wouldn’t let him.  He simply looked pleadingly at Carol for a moment, not enjoying the cruel smile on her face at all.

“Go!” she ordered in no uncertain terms.  And Roger found himself turning and opening the door, and leaving to go shopping… with Jennifer.

He was already late.  He knew that.  But Carol had made him late.  Carol and her cruel games.  He dreaded pulling his truck into Jennifer’s driveway.  He dreaded letting her see him dressed as he was even more.  And he certainly wasn’t looking forward to going shopping dressed like this either!  Carol hadn’t even given him a chance to grab a jacket before he left the house.  A jacket might have hidden his larger breasts at least a little bit. 

As he parked his truck, he saw Jennifer rushing out of her door to meet him.  She ran to his truck and stopped next to his door instead of going around to the passenger side to get in.  He rolled his window down.

“Why don’t we take my car?” she asked.  “That way I don’t have to climb…”  And then she stopped speaking for a moment.  “Are you wearing makeup?” she asked.

Roger felt his face growing red.  “Just a little,” he admitted.

Jennifer wasn’t sure what to think about that, so she forced herself to smile.  “Nice,” she said… even though she couldn’t really see it that well.  “Anyway… let’s take my car.”

Roger had a lot of grave misgivings about letting her see the way he was dressed, but he knew she was going to see him one way or another.  Slowly, he opened his door… and grabbed his purse… and let his high-heeled feet slide down toward the ground below.

“Roger,” Jennifer exclaimed, “you wore your other shoes too?”  But as he got further out of his truck, she now couldn’t help but notice his larger “breasts.”  And you’ve certainly padded your top a lot more as well!  To tell the truth, the bigger size looks a lot better on you.  Your other bra was much too small for your frame.”

“Uh… thanks,” Roger replied sheepishly as he stood there and let her look him over. 

“So… I take it this is all you have other than your one dress?” she asked.

“Pretty much,” Roger replied.

“And you decided to wear all of it this time?” she asked.

Roger just shrugged. 

Jennifer continued to look him over.  He looked ridiculous!  But if he was willing to go out in public looking like this, then maybe he really was serious about becoming a woman… eventually anyway… because he had a very, very long way to go!  “You look silly,” she said.

“I know.”

“But… at least I guess, you tried.”

Roger said nothing again.

Feeling somewhat unsure about being out in public with him, Jennifer turned toward her car.  “Let’s go,” she said.  “I like your purse by the way.”

Roger declined to thank her for the comment.  He felt foolish enough.

“Did you tell Stan?” Roger asked as soon as she had backed out of her driveway.

“Tell him what?”

“About what I’m doing?” Roger asked.

It was a short moment before Jennifer replied.  “Yes.”

Roger wasn’t happy about that.  But he knew it would be inevitable.  More so after tonight.  “I’m kind of hoping this doesn’t get out too soon,” he said.  “It wouldn’t be good for the kids to hear about this before school gets out.  After that… I won’t be there anymore.”

“I’ll let him know,” Jennifer replied.  “But I don’t know if he told anyone else already.”

“Let’s hope not.”

“Where to?” she asked brightly, trying to lighten Roger’s seeming gloomy mood.

“I don’t know.  You probably know better where to shop than I do.  I’d rather not be too close to home though if possible.  I’d rather not run into anyone I know.”

That made sense to Jennifer.  Besides, she wasn’t sure she wanted anyone she knew to see her with him!  She headed for Gainesville instead of anyplace closer.