The Housekeeper - Chapter 28 Part 1 of 2

The Housekeeper

By Karen Singer

Chapter 28 Part 1 of 2

Roger was really hoping that he would be able to start cutting wood and constructing the Whittaker’s deck itself next Saturday, but between the rain and Stan… and the rocky ground, it wasn’t looking like he would make it.  So far, he was only half finished digging the holes for the footings.  To solve that problem, he asked Janice if she minded if he started going out to work on the deck every day after school.

“I have no problem with that at all, Mr. Brinkley… just as long as you are dressed properly each time you go out there.  However, since I am working hard here every day to prepare a decent meal for you in the evenings, then I expect you to be here every day at dinner time to eat it.  Six o’clock, Mr. Brinkley.  I will expect you to be home every evening by six o’clock for dinner.”

All that Roger’s mind could conjure up about eating dinner though, was having to eat it like a dog on the floor.  Her time seemed a bit early considering the work he had to do, but otherwise, he had no problem with it.  He nodded.  “Thanks.  I’ll be home by then.” 

He went to his bedroom and changed into his working clothes… including the stuffed out bra and the boots he had shined again last night before going to bed.  At least he’d have a little while each day to make some progress on the job… and he’d be further away from Janice for that bit of time as well.  He had no doubt however that every evening after he ate his dinner, that he would be expected to continue making more “progress” toward becoming a woman.  And with nothing better to do in the evenings, he was fairly certain that he would be getting in plenty of practice with his new abundance of makeup supplies.

He drove out to the Whittaker’s house and went straight back to the backyard to go to work… not even bothering to let them know he was there.  Twenty minutes later, the skies opened up and the rain began pouring down on him.  And despite the dregs of a cold he was still nursing through, he ignored the rain and continued to work.  It wasn’t just that he didn’t want to go home to where Janice and Carol were, it was just that his mind was too besought thinking about things.  And one of the main things that preoccupied his mind was Jennifer… and Stan. 

The last time he had been out here, Stan had shown up.  How the hell did he figure out how to get here?  And Stan was overly concerned about him?  He really wished that Stan would have just stayed away!  It was too dangerous.  Not to mention too embarrassing for him.  And now Stan knew about his stupid little breasts he was supposed to have while he worked the jobs as well.  That wasn’t just embarrassing, it was troubling!  Troubling because now obviously Jennifer knew about it too!  Those two were suddenly awfully chummy lately.  Why?  But he didn’t want to dwell on the why of that one too much.  He had a sneaking suspicion as to why they were so close lately, and he wasn’t all that happy about it.  Especially since Jennifer had simply dumped him.  Right out of the blue – dumped him!

And now both Jennifer and Stan were on his case – a little too much.  They were both way too concerned about him.  And that spelled trouble!  He did suppose that if either of them were acting strange, that he would do everything he could to help out in any way possible.  That’s what friends did!  So he supposed he should be grateful.  But the situation had him caught between a rock and a hard place.  Thanks to Janice, he literally couldn’t tell them anything at all about what was really going on… and at the same time, the more they poked into his problems, the more afraid he became – for them!  It wasn’t safe!  But how could he explain that to his… friends.  And they were without a doubt – friends.

He worked in the rain as long as he dared.  And by the time he climbed back into his truck again, he was soaked to the bone and starting to feel like his cold was coming back full force again.  Not good.  He hurried home, where Janice berated him terribly for not having the common sense to come in out of the rain. 

“Carol…” Jennifer called as her early morning art class was about to end.

“Yes, Miss White?” Carol replied.

“Can you stop by my desk for a minute after the bell rings?”

“I guess so,” Carol replied uncertainly.

A moment later the bell sounded and everyone started filing out of the room.  And Carol stopped by Miss White’s desk.  “You wanted to see me?” she asked.

Jennifer crooked her finger to get Carol to move over closer.  “I understand that you have some pictures of Mr. Brinkley getting a makeover after a dare,” she said softly.

Carol’s eyes widened in shock.  “You heard about that?”

“I think everyone has heard about it,” Jennifer replied.

“That wasn’t good news for Carol.  If her mother ever found out, there would be hell to pay!”

“Uh… yeah,” she replied uncertainly.

“Can I see them?”

“You want to see them?”

“That’s what I asked.”

Carol shook her head.  “It may not be a good idea.”

“Why not?  You let all your friends see them.”

“Yeah but…”

“Please?” Jennifer asked.

“You won’t tell Momma about them, will you?”

Jennifer was totally surprised by that request.  “No, I won’t tell her.  I promise.”

Hesitantly, Carol found her cell phone and turned it on.  A minute later she was scrolling through the pictures on it until she got to the ones for Roger’s makeover in the store.  She was very careful not to let Miss White see any of the earlier pictures on her phone!  She showed her two at the beginning… then the last three pictures. 

It was all Jennifer could do not to laugh when she saw them.  But she had to admit, he did look fairly good at the end.  Surprisingly good!  “Any chance I can get a copy?” she asked.

“I don’t know,” Carol replied.  “I really shouldn’t have shown them to anyone.  That was probably a mistake.”

Jennifer nodded.  “Maybe, but it’s all over with now, so what’s the harm in letting me have a few of them?”

With a few misgivings, Carol finally agreed. And a few moments later, she hit the button to send five of the pictures to Jennifer’s cell phone.

“Thank you Carol.  And I promise not to tell you mother anything about it at all.”

Carol was relieved as she hurried out of the room and on to her next class.

Jennifer watched Carol running out of the room.  She had been very concerned about her mother finding out.  She had mentioned that showing the pictures might have been a mistake.  Something told Jennifer that there was more to the issue than she knew.  She had promised Carol that she wouldn’t tell her mother about the pictures.  But she hadn’t promised not to tell… or show them… to anyone else… like Stan… and then Roger!

“Geez!” Stan exclaimed softly as Jennifer showed him the pictures she had gotten from Carol.

“Yeah,” Jennifer replied, “But you’ve got to admit, he looked surprisingly good at the end there.  Whoever did the makeover on him, did a really good job.”

Stan just shook his head.  “Something is going on there with him… and every time we turn around, it gets worse!”

“Yeah, it does,” Jennifer agreed as she put her phone away. 

Together, the two entered the cafeteria line to get their lunches.  As they entered the back of the line, they could both see Roger just paying for his lunch and leaving. 

“What do we say to him?” Jennifer asked.

“Who knows?” Stan replied.  “Does he know that everyone is talking about those pictures?”

“He must!” Jennifer replied.  “If I heard about them… and you heard about them, how could he not know?”

Roger knew he had to find somewhere else to have lunch… he knew it just as soon as both Stan and Jennifer set their trays down at the same table where he was eating.  And he immediately started worrying about how painful his cock was about to get.  But surprisingly, he barely felt anything from it this time.  He supposed that was because he was simply too worried about his friends… and annoyed that they wouldn’t leave him alone.

He saw Stan sit down, but Jennifer set her tray on the table, then hung her purse on the back of her chair… and then came around the table behind him.

“These are absolutely… priceless!” she exclaimed as she started finding the pictures on her cell phone.  She leaned over his shoulder and held the screen in front of him. 

The quick sexual rush from Jennifer leaning over him… and the cold aching in his cock because of it… vanished in an instant as Roger saw the first picture – and he recognized one of the first ones that Carol had taken of the makeover he had gotten.  “Where… did you get those?” he managed gasp out as Jennifer flipped to the next picture.  There was no way that Roger could take his eyes off of the screen.

“Wait a minute!” Stan interjected before Jennifer could reply.  “You mean, you didn’t know about those pictures?”

“I knew that Carol was taking them when it happened,” Roger replied, still totally in shock as he now looked at his face… or really… the female version of his face.  “But how did you get them?” he asked Jennifer.

“I asked,” Jennifer replied as she carried her phone around to the other side of the table where her tray was.  “Actually, I had to plead a bit to get them… and agree not to let her mother know I had seen them.”

Roger’s head was spinning a bit.  “But how did you know about them in the first place?”

Both Stan and Jennifer looked at Roger incredulously.  “You mean, you didn’t know that probably every kid in the school… and most of the teachers as well, have either seen those pictures… or they know about them?”

Roger’s jaw dropped.  “Every…kid?” he stammered.

“As far as I can tell,” Stan replied.

Roger looked to Jennifer, who just nodded, then leaned closer.  “So… who dared you to do it?” she asked excitedly.

“D… dared?” Roger asked.

“That’s what Carol told everyone.  You did it on a dare.  So… who dared you?  Was it her?”

“Wait a minute!” Stan interjected again as he looked at Roger’s shocked face.  “You mean, this wasn’t done on a dare?”

Roger started to shake his head… then thought better of the idea.  “Um… yeah, it was.  Totally!  I just didn’t think anyone else was going to find out about it.”  He was relieved to see Stan sit back and seem to accept that.

“Well, I guess the cat’s out of the bag now,” Jennifer replied as she started eating.  “So who dared you?” she asked again, this time with her mouth full of food.  That new housekeeper of yours… Carol’s mother?  I’m only guessing that because obviously Carol was there to take the pictures.”

“Uh… yeah, it was,” Roger agreed, hoping that the “dare” angle would hold up.

“Why’d you do it?” Jennifer asked as she shoved more food into her mouth.

“What do you mean, why?”

“What brought up a crazy dare idea like that in the first place?  And damn, I wish I had been there to see it!”

But Roger wasn’t at all sure how to answer that question.  “Uh… I don’t know.  It just kind of came up.  You know how these things go.  We got to talking about something I guess, and… one thing led to another.  Something like that anyway… I guess.”  He was glad to see Jennifer nod as she continued eating.  He did his best to continue with his own lunch, but his stomach was so tied up in knots, it was difficult to get anything down.  All the kids knew!  And most of the teachers too?  Evidently… the whole school knew about that makeover! 

And one other tiny little thought finally registered in his shocked brain – Jennifer had said she had to plead with Carol to get the pictures… and then agree not to let Janice know she had seen them.  Carol had been afraid of her mother finding out! 

“I think he was lying,” Stan said as soon as Roger had left the table.

“About what?” Jennifer asked.

“About that makeover being done on a dare.”

“Obviously,” Jennifer agreed.

If Roger had any doubts about all the kids knowing about his makeover, they were all put to rest by one of his students in his last class of the day.  “Hey Mr. Brinkley,” the kid had called out just before the period had started.  “You looked awesome as a woman!”

Roger’s face turned beet red as all the other kids in the class laughed.  Yeah, there was no doubt, everyone knew.  Everyone!