The Challenge - Cover

The Challenge

Copyright© 2008 by Openbook

Chapter 2

Drama Sex Story: Chapter 2 - The 29th story in the Caddymaster series. Jackie finds himself faced with an ethical dilemma. Will he give in to his worst side, or will he somehow manage to rise above temptations and do what he knows he should?

Caution: This Drama Sex Story contains strong sexual content, including mt/ft   Teenagers   Consensual   NonConsensual   Reluctant   Heterosexual   Incest   Brother   Sister  

I was already sitting in the kitchen half an hour before Dan was due to come by to get me. My mother was up too. She had gotten up to make my father's breakfast and to pack him his lunch. She had stayed up after he left, trying to get things organized for breakfast for my brother and sisters, after everyone else got up later in the morning.

We were both talking quietly about Kathleen Noonan. I'd mentioned to her that I'd be working on lawns and doing windows for Dan Noonan, and watching out for his sister too. I told her about the conversation I'd had with Dan's father. I also told her that Kathleen seemed to be acting inappropriately around Dan and me, telling her about the nipple pinching business.

"Jackie, you have to be very careful about appearances in these kinds of situations. That poor girl. You need to understand that she isn't able to think things through for herself. You have to resist any temptation you might have to take advantage of her."

"I don't have any temptations like that, Ma. I just was wishing that I didn't have to watch out for her. If I was planning on doing anything with her, would I be sitting here telling you about what had already happened?"

"You're becoming a man now, Jackie. Men have a tendency to not think about the consequences for their actions. They act without giving much thought to how much harm can come from what they're doing. I hope you wouldn't do anything to bring shame down on our family."

I was going to tell her not to worry, to assure her that I'd never do anything like that, but Dan picked that time to start climbing the porch stairs. I got up instead, crossing over to the door to go outside with him. We walked over to the truck and I said hello to Dan's cousin. Frank Leahy was about seventeen years old. He had real dark hair, kind of like mine, and was darker skinned than both his cousins. He was the same age as my cousin, Billy, but the two of them definitely ran in different social circles. Kathleen was sitting in the truck bed. She smiled at me and gave me a wave with her hand.

We drove about two miles to the main job for the day. It was a big house over by the golf course. It was a single story house, but it was big. The front lawn was at least a hundred feet wide and about another hundred and fifty feet long. There was a driveway going all the way up, but that just meant there was a lot more edging that needed to get done. I helped Dan unload the truck bed and he and I went off to get the water buckets filled for Kathleen. Frank Leahy just sat in the truck, not even offering to give us a hand with anything.

Dan had an old milk box that he set up for Kathleen's use. She wouldn't climb ladders, but she didn't mind standing on the overturned milk crate to help her get higher up on the windows. I watched as both Dan and Kathleen demonstrated how they cleaned the windows. They used a vinegar solution with old newspapers to clean off any stains on the window, then used a rubber scraper with clean water to finish the job off. I was impressed with how clean this got the outside part of the windows. Dan told me that they didn't do inside windows, only outside.

Dan took me over to his lawn mower and watched as I filed a new edge on the mower blades. Once he was satisfied that I really knew my way around his lawn care equipment, he and Frank left. He told me that they'd be back at around eleven thirty or twelve, saying that this should give us plenty of time to get things done before they gave us a ride over to the next job. I wasn't so sure. I'd never mowed and edged such a large lawn before. There were about fifteen trees on the front lawn too, and they'd all need special care when it came to edging and working around the roots at the bottom.

Right after Dan and his cousin left, I got busy with the mower. I kept one eye out for Kathleen as I proceeded. She appeared to be working just like she was supposed to. I'd see her progressing from one window to the next until she was already over at the one farthest from the side of the lawn where I was doing my mowing.

A little bit later, when I looked over to see how she was doing, she had disappeared from my view. I decided to take a little break to go check up on her, to make sure that she was all right. I found her on the far side of the house, leaning back against the building while sitting down on the milk crate. The top buttons on her jeans were opened up, and her hand was inside her undies as she played with herself. Her other hand was at her breast, pinching and pulling at her nipple. Her eyes were closed tight and all scrunched up as she strummed her fingers inside her panties. She was absolutely oblivious to anything other than the pleasure she was giving herself.

As quickly as I could manage it, I turned myself around, heading back the same way I had come, hurrying back to my mower. I hadn't paused to try to get a better look at what she was doing. All I wanted to do was finish up this job and leave there. I hadn't found anything exciting about what she was obviously doing. Instead, I felt a wave of anxiety and worry. This girl was a lot different than any other girls I'd ever been exposed to.

She seemed oversexed to me. I wanted to make sure I had finished up all the mowing and edging by the time Dan got back. When that happened, I was going to tell him that I couldn't do this for him anymore. Things would have been fine if it hadn't been for his sister, but I knew she was heading for big trouble, and I didn't want to let myself get caught up in it.

I was finished mowing and edging before eleven o'clock. By then, Kathleen had finished up the front and back windows and one side. I checked all the windows she'd finished before giving her a hand with the last side of the house. I'd do the vinegar and newspaper cleaning and then, Kathleen would use the rubber scraper and clean water to finish things off.

By the time Dan and Frank showed up, at eleven thirty, we were all finished, and all our equipment was stacked up and ready to be loaded back on the truck. Kathleen and I did the loading while Dan went to check over the job we'd done.

Frank stayed behind the wheel of the truck, obviously not thinking he should be out giving us a hand. After Dan finished checking up on us, he went to the front of the house and rang the doorbell. An old man came out and he and Dan made a circuit of the property before returning to the front door and both going inside the house. A minute later Dan came out, smiling. He and I both got in the cab of the truck and started driving over to the next mowing job. I knew that this was a small lawn job, and that the other three would be returning to Dan's house for lunch while I did the work.

"Three dollar tip for the lawn, Jackie. You and Katie split another three for the window cleaning."

"She should get the whole three for that, Dan. I only helped her a little bit, at the end. She did all the rest."

I was damn happy to get a three buck tip for cutting the grass. I also wanted to try to be fair. I could see that Dan was very pleased by what I'd said.

"All right, if you're sure? Katie will be real happy getting to keep all the tip money herself. She does a good job too, doesn't she?"

"I only checked on her once before I finished up and came over to help her. When I checked on her, she seemed to be enjoying herself, so I just left her to it."

"This next job is very small. Front and back should only take about an hour. We'll go eat and come back to get you at about quarter 'til one. The last mowing job is close to the last window job. It isn't very big either, but the lady who owns the house is very particular about the edging around her little flower garden. I usually use shears on it. If you do a real good job, she usually gives a two dollar tip. She likes it if you rake up inside the garden too. She sees fresh rake marks around her flowers, that almost guarantees she'll be happy with the job you did. This job you're going to do now, don't try to do too much with it. He never even comes out to check, and we get a buck tip either way."

I did the math in my head. Six bucks for doing the mowing, and another six dollars in tips. That was damn good money for a fourteen year old in 1956. My earlier decision to just quit after that first day needed to be given more thought.

When they dropped me off at the second house, Dan got out to help me unload the lawn tools. Frank and Kathleen stayed where they were. When we were bringing tools up to the yard and were about twenty yards from the truck, Dan asked me about Kathleen.

"Did Katie do anything to act up over at that last job, Jackie? The reason I'm asking is because she has that look she sometimes gets when she's been up to something."

"She was fine. The only thing I noticed was she did that thing she does, that touching herself thing? She doesn't seem to care too much about who sees her doing that."

"She has this self control problem. Did you tell her to stop it?"

"No. I turned around and went back to my mowing. Even talking to you about it is making me pretty uncomfortable. I think your family is going to have big problems with her if she keeps on doing things like that out in public. Sooner or later, someone is going to see her doing that and try to take advantage of her."

"We know. We watch her as close as we can, but you can't watch her all the time. Last night, she snuck out of her room. She was gone for at least two hours."

"I saw her when I was going back home. She asked me if your dad said it was okay for me to work with her today. She was pinching herself then too. She also said she wanted to show me what you like to do to her. I didn't let her."

Dan's face got very red when I said that last part. Normally, I wouldn't have told him about what his sister had said. I guess I felt bad for him, and wanted to give him a little warning. It had to be tough trying to take care of a sister who was acting like Kathleen did. That didn't mean he should do things with her though. Maybe, if he knew she was telling people things about what they did, he'd quit doing them. That's what I hoped when I told him what she'd said.

"It isn't what you're thinking, Jackie. There is a little game we play, whenever I need to get Katie calmed back down again. She has a much higher than normal sex drive. A lot of the slow people seem to have that. Sex is a basic need, and Katie is going through puberty now. For her, it has hit harder than it does with other thirteen year old girls. She doesn't know how to hide it yet. Really, she doesn't even know that it should be hidden. All she knows is that it feels good to her. All I'm doing is hugging her, and holding both her arms so she stops doing what she shouldn't be doing. After I do that for a few minutes, she gets calm again. It's all very innocent. I wouldn't ever do anything to hurt her."

After Dan left, I thought about what he'd said. He sure had seemed sincere in what he was telling me. Maybe I'd just jumped to the wrong conclusion earlier. Whenever I'd seen him with his sister, he'd looked like he loved her and was trying his best to take care of her. The idea that I would be giving up an extra twelve dollars a week might have had something to do with getting me to lean more towards Dan's side of things than I might have otherwise.

I finished up the lawn job in about forty minutes. I spent the time I was waiting for Dan to get back using the shears to trim some of the grass in and around the thick boulder wall he had all along the right side of the property. I had almost finished when the truck pulled up to get me. Rather than go over and help Dan with loading up the lawn tools, I finished up that last little area I still had left. I had just gotten finished when this old man came striding out of the house, heading straight for me. He didn't look happy at all. I didn't know what I might have done wrong.

"I'm not paying any extra for what you just did. I didn't ask you to do that work."

"I didn't expect you to. I had a little time before Dan came back to get me, and I wanted to see if I could make that wall look a little better. That's a pretty nice wall."

"My father and I built that wall before your own father was born. Didn't use any mortar to hold it together either. Every stone was made to fit. All natural like. Don't see many walls like that anymore. Every stone came from right here on our property too."

"I think it looks better now that it's trimmed up a little. Makes it seem higher too. You might want to get some weed spray and put it in some of the cracks where things are growing. It would kill off that moss and make the whole thing look nicer."

"Do you know how to do that? How much would it run me if you were to do that?"

"You'd have to ask Dan those questions. I don't think it would cost too much though. He could probably get the whole thing done for you the next time he comes out to mow your lawn. I'm just helping him out a little today."

The old guy went over to speak with Dan, and then the two of them went up to the house. Five minutes later, Dan came out holding a check in his hand. Again, he was smiling.

"Five dollar tip, Jackie. Most I ever got from him was a buck. He told me he'd pay an extra twenty bucks next time if you came by and did what you said to his wall when you cut his grass. What did you tell him you'd do?"

"I just suggested he should get some weed killer and spray where things are growing inside his wall."

"What is this weed killer?"

"I don't know. That's what my father calls it. He brings it home from the sub base. He puts it in a mosquito sprayer and sprays it around the base of our house. Whatever he sprays it on, it's dead in a day or two. He calls it weed killer. It's some kind of liquid chemical. I can get some from him if you want me to."

We drove out to the last mowing job and they dropped me off again. Dan took Kathleen a few houses over and helped her get started on the windows there. From where I was, I could see her working. It didn't take long to cut the grass at this new place, and I took my shears out to do a careful edging around her garden. I also decided to square up the edges, because that hadn't been done in awhile. After I was done, I raked out the interior of the flower garden and cleaned around each of the flower beds. When I got done, I took all the lawn tools out to the side of the road and went over to see if Kathleen needed any help. She had already finished by the time I got there.

"Dan said I get to keep all the tip money from that first house. He told me you said that was fair."

"You did almost all the work by yourself. I didn't have to do very much. This time you got it all done before I even got here. Good work."

"I'm good at doing things once I know what to do. When Dan was trying to teach me, it didn't go that good at first. Now I'm faster. Aren't you even going to check the work I did?"

"I don't see why I should. You've done more windows than I ever have. Dan will probably check it when he gets back. He checks my stuff too."

"I saw you looking at me over at the other house. When I was tingling my winkie." Kathleen had this open grin on her face. It seemed to please her that she'd known I'd seen her playing with herself.

"I saw you were taking a break and didn't want to disturb you."

"I was thinking about you when I was doing that. It makes it better if you think about someone. Do you think I'm pretty?"

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