The Challenge - Cover

The Challenge

Copyright© 2008 by Openbook

Chapter 1

Drama Sex Story: Chapter 1 - 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  

It was late in the summer of 1956. I was fourteen years old, and still spending all my summer day's caddying out at Shennecossett Country Club.

Dan Noonan was someone I'd known for most of my life. We weren't exactly friends, but we weren't enemies either. He was a few months older than me. Red haired and freckle faced, with a fair complexion and a ready smile. He had three sisters, two older than him, and Kathleen, who was a year or so younger.

Dan's father worked as a fisherman, and his mom worked in an insurance office over in New London. Like our family, the Noonan's lived in the projects. Dan did some caddying too, but mostly he made his money by mowing the lawns and cleaning the windows for the rich people who lived in other parts of Groton.

One of the reasons Dan didn't spend all his days out caddying at the golf course was because he had to watch his kid sister at least two or three days a week. Kathleen could go with him when he was out mowing lawns and cleaning windows, but she wasn't able to be with him while he was caddying.

Late in August, right after I came home from the golf course, Dan approached me, wanting to know if I'd be interested in helping him out with a new work project he was trying to get started with his cousin, Frank Leahy.

"I only have Monday's off, Dan. The rest of the time, I'm out carrying bags on the course. What would I be doing?"

"Frank has his driver's license now, and my pop says we can use his truck whenever he's out on the boat. We've been getting jobs cleaning out basements and cellars, hauling away people's trash to the dump. A lot of people have stuff they want to get rid of, and they'll pay us to take it away for them. Mr. Penny, over at the dump, he pays us for some of the things we bring him too. I still have my regular lawn and window accounts to take care of though, and there isn't enough time to do them and still be able to do the dump hauling business too. Plus, there's Katie. My father says she still needs to be watched on my days, and I can't take her with us in the truck. You could help me out on Mondays, Jackie."

"You want me to baby sit your sister?"

"Naw. Katie helps me with the window cleaning business. She does all the low stuff, and I do anything too high up for her to get at. She won't get on a ladder. I pay her just like she was a regular employee. You can do my mowing jobs and help her out with the high stuff on the windows. That way, someone would be keeping an eye out with her, and I could still work with Frank on this other thing."

"How much would you pay me?"

"I'd give you six bucks a day, and you get to keep any tips they give you for the mowing. For the windows, you and Katie would both have to split the tips."

I wasn't making anything on Mondays, because the golf course was closed on that day every week. They needed to close it so the grounds keepers could fix it up after all the weekend golfers had finished playing their rounds. I was saving up for a car, so an extra six bucks or so a week sounded pretty good to me.

The problem I had was with having to look after Dan's sister. Kathleen Noonan went to a special school that was run by the Catholic Diocese for kids who were slow learners. She looked normal and everything, but she had been born retarded. You couldn't tell right away, not when you first met her, but after being around her for a little while, it was pretty easy to see that she had something wrong with her brain. She acted like a little kid who hadn't grown up yet.

She was almost the same age as my sister Joan, but she mostly played in the neighborhood with all the younger kids, the eight and nine year old's. She looked kind of like all the other Noonan's, red hair, freckles and fair complexion. All the other Noonan kids were at least normal when it came to having regular brains and doing well in school.

"I don't think I'd be good at watching out for Kathleen. I don't know much about looking after people like her."

"What's that supposed to mean, Jackie? Katie doesn't need anything special. All you have to do is keep an eye out to make sure nobody tries to bother her. She knows how to do what she needs to do. You just make sure she gets to where she's supposed to be, and then see that she has everything she needs to get the job done. Help her to get her buckets filled with water, and make sure she has her window scrapers, vinegar, and plenty of old newspapers."

That was another thing about all the Noonan's. In spite of them having sent Kathleen to a special school, they pretty much wouldn't admit there was anything the matter with her. Never mind the fact that most thirteen year old girls didn't have someone watching out for them every minute of the day like she did.

"How about if I just cut the lawns for you on Monday's then? You can get someone else to watch out for your sister."

"Why don't you help me out here, Jackie? Summer's almost over anyways. This new thing, we can do it on weekends, even after school starts up again. Watch her for one day and see if she causes you any problems or not. Most of the time, she doesn't need any help from anyone. She gets nervous though if someone she knows isn't around where she can see them."

"Okay, I'll try it on Monday. Six bucks plus tips. How many lawns do you have for next Monday?"

"Three lawns, and only two window cleaning jobs. One of the lawn jobs is a big one, but we're doing their windows on Monday too, so you'll be right there with Katie for about three hours. You'll see, she isn't any trouble for you at all."

This was on a Thursday that we had this conversation. By Sunday night, I'd pretty much forgotten that I'd made the commitment to Dan. When he came over to our place and knocked on the screen door, it all came back to me in a hurry. I got up from where I'd been sitting in the living room and answered his knock.

"Hey, Dan. We still all set for tomorrow?" Dan was up on the stair stoop, and when I opened the screen door I noticed Kathleen standing at the bottom of the steps. "Hi Kathleen, how you doing?" I didn't really know her that well. I'd known her all her life, but we hadn't ever hung around together. She used to play Kick the Can with the other neighborhood kids, but she was always one of the first ones caught. She wasn't very good at hiding, and didn't run very fast either. I could see her face blushing when I said hi to her.

"Jackie, I was wondering if you'd mind coming over to our house to speak with my parents? They want to make sure you're all right to be working with Katie and me." Dan was trying to be diplomatic, but I could tell he'd probably just sprung his new idea on his parents, and they wanted to make sure I wasn't going to be trying to take advantage of their daughter. I had lived with my own parents all my life, and I already knew how embarrassing they both could be. I already knew Mr. Noonan a little bit, but I didn't remember ever meeting Dan's mother before. My parents weren't social butterflies. They took a lot of getting used to, and my Dad's temper and volatility often made all our neighbors want to keep their distance.

"Now?"

"If you wouldn't mind. My father is leaving at three in the morning, and he wants to make sure you're okay with all of this. It shouldn't take too long, please?"

I looked down at Kathleen before answering. She was staring at my face, with both her arms crossed at her chest. It looked like she was trying to hide her breasts from me. I didn't think she had any. I hadn't noticed her in awhile. Her arms folded like that just drew my attention to her chest, and I could see that she had grown some boobs. They weren't very big, not like Joan's, but there was definitely some chest development going on there. While I was looking at her, she looked like she was pinching herself, right on her boob, with her thumb and index finger. I turned back to Dan to tell him I'd go with him, but he was looking down at his sister too.

"Katie, remember what mama told you about doing that?" As soon as Dan spoke, Kathleen stopped pinching herself and unfolded her hands before turning away from her brother and me. "Sorry, Jackie. Sometimes she does things like that. It doesn't mean anything." Hearing what he was telling me, Kathleen turned back around and called her brother a bad name.

"Danny's a 'shit face'." I didn't know how I was supposed to react at that. I'd gotten into plenty of arguments with my brother and sisters, and we'd ended up calling each other names too, but not one like that. Usually it was either 'bastard' or 'son of a bitch' we'd call each other. 'Shit face' was a new one on me. It wasn't the sort of thing you'd expect to hear from a girl either, especially not a thirteen year old girl.

"I'm going to wash your mouth out with soap when we get home, Katie. Do you remember what I told you about using those words?" Dan seemed upset, but not too surprised by what she'd said to him. For some reason, I got the idea that Kathleen had done things like this before. Maybe it was part of her being retarded? I didn't know. I remember thinking that my father would have washed out Joan's mouth with soap too, if she'd ever dared say that in front of him.

"Maybe this isn't a good time for us to go talk to your folks Dan. Kathleen might be upset now, and I wouldn't want to make things worse."

"Jackie, don't worry about that. Katie has been doing things like this a lot lately. The Nuns all say its only a phase she's going through right now. She doesn't like people bossing her around, so she acts out when she gets mad about things. My parents won't let you do this if you don't come see them tonight."

"That's okay. I wasn't all that sure about trying this anyway. Maybe you can stay with Kathleen tomorrow, and I can work with Frank instead?"

"We have a deal, Jackie. You said you'd give this a try."

"I have to go pee pee, Danny. We need to get home now." Kathleen was pressing the open palm of her hand between her legs. Her dress was bunched up in front from the way her hand was. Little kids did things like that, not thirteen year old girls. All kinds of thoughts were running through my head about how embarrassing having a sister like Kathleen had to be for Dan, and for his other two sisters.

I turned back to Dan and told him he needed to look after his sister. When I was finished telling him that, I opened up the screen door and went back inside our house. Not more than two seconds after I went inside, I heard footsteps on my porch, and Kathleen came right into our house and headed straight for our bathroom. She was lucky that the bathroom was empty, because only a second after she shut the door, I could hear her peeing.

When she came out, a minute or two later, her face was beet red with embarrassment, and she hurried past me out of the house and down the stairs.

"Jackie, please come with me to talk to my parents?"

My father had gotten up out of his overstuffed chair and was heading towards me with his newspaper in his hand. The last thing I wanted to do was try to explain to him what was going on. I turned myself and went back outside again.

"Pop, I'm going over to Dan's house to see about a job I'm supposed to do with him tomorrow. I won't be long."

"Who was that girl, Yutch?" My father was about five feet from the screen door when he asked me that question.

"That was Kathleen Noonan, Dan's little sister. I told her she could use the bathroom. I'll be back in an hour, okay?"

My father came up to the screen door and looked Dan over before saying anything to me.

"Everything's okay, Yutch? You aren't getting into any trouble, are you?"

"It isn't anything like that, pop. I'm going to be mowing some lawns for Dan tomorrow, and he needs to tell me where to go and show me where everything is. Tomorrow he's doing some different work with his cousin. I'm just helping him out for a day. Nothing that's going to cause anyone any problems."

"See that you're back here before ten, Yutch." My father kept himself framed in the doorway, watching as Dan and I hurried away, trying to catch up with Kathleen, who was striding purposefully towards her own house.

"Your father scares me, Jackie. Is Yutch your real name? I thought it was John?"

"He scares me too, Dan. No, for some reason he calls me that name. I don't know why. I think he likes the way it sounds. I used to think he did it because he couldn't remember my real name, but his name is John too. I'm a junior. I don't know why he calls me that, he just does."

"My father says your father might be crazy." Dan said that without thinking about it first. I could tell this because of the face he made once he realized what he'd just said.

"He might be. He was in the war. He went to Korea too. Sometimes, I wonder about him too. He isn't like other people's fathers. He gets in lots of fights, and he doesn't care about what anyone else thinks. If I told him about what your father said, he'd go over to your house and beat your father to a pulp."

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