Chapter 1

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Cheating, .

Desc: Sex Story: Chapter 1 - The seventeenth story in the Caddymaster saga. Jackie gets led by Ray into a new business venture and into exploring some of the family traditions.



It was sometime in 1966 that I started getting the strong feeling that my father was very disappointed in me for not joining one of the armed services. He didn't exactly say anything to me directly, but he had made several comments when I was around him, knowing that I had to have heard them. He had served in the Navy for twenty years, being loaned out to the Army for most of World War II and the Korean Conflict due to his photographic skills and experience as a combat photographer. He was proud of his military service, and had very little respect for the men who'd chosen to sit the War out and who had spent the War safely at home. With Viet Nam getting bigger and bigger, he couldn't understand why I wasn't just itching to get into the Navy or Marines, and get my share of the family glory. My father had been badly injured in World War II, and his brother, my Uncle Paul, had almost lost his leg when he got stitched with machine gun fire in the back of his right knee in Korea. Uncle Ray, my mom's brother, had died while in the service during the Second World War, in a freak, drunken accident. Uncle Donald and Uncle Sonny were both in the army and saw action in the second war too. I wasn't interested.

Ellen and I were visiting with Lenny and Clara one day when it all came to a head with my father. Of course, he'd been drinking before he stopped over to give my Aunt Betty a message from my mother. Seeing me there, I guess he was starting to worry that his comments about shirkers and draft dodgers had been too subtle for me. "Yutch, when in the hell are you going to step up like a man and enlist to fight for your country?" I just looked at him, not really wanting to get into it with him, but not content to just sit there and let him give vent to his displeasure at my lack of patriotism either.

"I figure you and Uncle Paul and Uncle Ray did enough for the family already, pop. I don't think I'll be signing up anytime soon."

"You think you're too damn good to serve your country? I've got two healthy sons, both of an age to serve, and neither one so inclined. I never thought I'd see the day when I had to wonder if I'd raised a couple cowards."

"I wanted to join up Uncle John, but mom and Clara said I couldn't. Because of my father and all." Lenny spoke up, hoping I think, to diffuse the tension that he could sense building between my father and I. Clara came over and put her hand on his shoulder, knowing that Lenny was sensitive to confrontations, and easily upset by them.

"Sure Lenny, I knew that you'd want to do the right thing, but you've got to take care of a wife and your children, not to mention your mother. Your cousins don't have any children to worry about, and their mother has me to take care of her."

"Pop, do you really think this is the right time and the right place to be getting into all this? I've never made any secret of the fact that I don't have any plans for joining up. I'm registered for the draft, so if they want me or need me, they know how to get in touch with me. I'm not going to volunteer though, no matter what you say."

"Yutch, I'm disappointed in you. Military service is a family tradition with us, on both sides of the family. In time of war, we serve. We don't wait to be drafted. We volunteer."

"John, my Ray was drafted, that's why he enlisted in the Navy, to avoid the Army. Sonny and Donald were drafted too. Didn't your brother get drafted too?" Aunt Betty had always resented losing her husband like she had. She was certainly no fan of military service for her son or nephews.

"Well, yes, Paul was drafted, but he was already planning on joining the Marines when he got his draft notice, so he went ahead and enlisted. Still, military service is a family tradition, drafted or enlisted. I expect both my sons to serve their country."

"I don't think they'd even take Ray, pop. Remember he lost his spleen that time? I think you've got to have all your body parts for them to take you. Maybe not your tonsils or appendix, but everything else. I think I'm classified as being in an essential industry too pop, so I don't think I'll be called up. If it makes you feel better going around calling people cowards, you go right ahead and do it. Of course, that name calling usually works both ways you know?"

"Are you saying that I'm a coward Yutch? Because if you are"

"No pop, you're certainly no coward, that's for sure. But you are something of a lush, and I'm sorry to see you getting all liquored up like you are right now, and then going around making an ass of yourself. As for me being a coward, well I don't think I am. I guess we'll just have to accept that we have a difference of opinion about that unless you want to continue calling me names and see where that leaves you?" Aunt Betty stepped between us right then, and Ellen and I left. I never was able to just disagree with my father. It always seemed to have to escalate upward until it finally boiled over into a mess. It was certainly as much my fault as it was his. I think it had to do with the bad memories I had about having to always back down and knuckle under to him when I was a kid. I don't remember there being any one specific time when I decided not to take any more abuse from him, but, by 1966, I was certainly in a low tolerance frame of mind about taking any more crap from him.

Ellen gave me a hard time for the entire drive back home. She held the opinion that I went out of my way to bait my father rather than ignore what he said and avoid getting him upset any further. I told her that my experiences had taught me that it would just keep escalating if I just ignored what he was saying. My father wasn't a man to back off when shown no resistance. Ellen's only frame of reference was her own father, a man who didn't like verbal arguments, let alone physical confrontations. She had never seen my father out of control before, so she didn't understand what was potentially involved with this latest fixation of my father's.

A few weeks later, Ray got his notice to appear for his draft physical. The timing seemed suspicious to me so I called Mr. Bennett about it and he told me that my father hadn't come to him about anything having to do with the local draft board. He told me that he could talk to a couple people and probably get Ray deferred if that was something that Ray wanted. I told him I'd let him know after I spoke again with my brother. I went over to see Ray and Sandy that night. Ray had already been visited by my father, and been ordered, in no uncertain terms, to do everything in his power to pass the physical and serve his country. In the end, my father pulled some strings and Ray was allowed to sign a waiver, giving the Army a hold harmless, releasing them of any responsibility for anything that might come out of him not having a spleen. It was the old boys network at it's finest, and in November, Ray raised his right arm and was sworn into the Army. He went to basic training in New Jersey and then went to a technical school to become a radio operator. In May of 1967 he shipped out to Viet Nam. My mother had somehow come across statistics concerning mortality rates for Army radio operators in Viet Nam right after Ray deployed, and she was very upset with my father.

Ray spent his whole tour in Viet Nam playing poker and trading in Kennedy half dollars and Levi's. He would have big boxes of small sizes of Levi's delivered from Travis AFB by military cargo plane and then he'd sell them in Saigon. He paid $3.80 per pair and sold them for $12 to $15 per pair. He did a brisk business in Kennedy half dollars too, selling them for $2.00 each. After he got back home, he would keep everybody laughing for hours with his outrageous tales of things he'd either done or seen in Viet Nam. He was attached to a rear echelon post near Saigon, working in a communications center. In spite of all the money he made in the Army, when he got discharged he was flat broke and in need of a job right away. I put him to work driving for me. I paid him more than my other drivers, even Lenny, because he needed more money. He was an operator, always on the lookout for a get rich quick scheme. Most of his schemes wound up costing him money for some reason. He worked as a driver for two years before he discovered something that he was good at and that would make him money.

Like my father, Ray had an eye for the ladies. The ladies also had an eye for Ray, also like my father. I'm sure that both of them had compartments of some kind that they kept separate from the rest of their life. Ninety per cent of the time Ray was a true blue, faithful husband. Ten per cent of the time he was pure alley cat. For some reason he always seemed to gravitate towards married women. One of these women, Alice Prescott, was a real estate broker in Groton. She was successful in her business too. It was 1971 when Ray started seeing her professionally as well as socially. Alice needed a dummy buyer for a property that she wanted to double escrow for herself. The land in question was a six acre parcel out west of Poquonnock on a dirt road. It didn't look like anything special, unless, and until, you knew that a major road was going to replace that dirt road within two years. Somehow, Alice was privy to that information, and chose Ray to be her dummy buyer. Ray's affair with Alice had been going on for about a year. They would manage to get away together about twice a month when Ray had one of his "overnight" deliveries. I never gave Ray an overnight delivery, and knew nothing about Alice or any of the rest of his little stable of married women.

Ray opened escrow as the buyer for this land, and everything would have worked out as planned if Alice's husband hadn't gotten suspicious about her involvement with Ray. She told her husband that Ray was simply a client of her firm and then told Ray that he'd have to handle the land purchase by himself since she was unwilling to risk having her marriage dissolve over a little fling that she had enjoyed. This left Ray with about thirty days to raise $6,000.00. It was an all cash deal and Ray had no cash, and hadn't written any contingencies into the offer. Alice declined to make him a loan. He was in trouble.

"Jackie, I've got something that's going to make the two of us rich! Instead of being like you and hogging it all for myself, I'm going to let you in on it. We'll go 50-50 on this, split it right down the middle." In the two years Ray had worked for me, he'd brought me an average of one can't miss opportunity every single week. So far, none of them hadn't missed. I'd invested in none of them either, since I was a little skeptical about Ray's judgment in that area.

"Thanks Ray, but you keep it all. I've already got mine like you said. You and Sandy can use more dough though, so you take it all, okay?"

"If you're sure then, all right, I'll keep it all. I'll need to borrow a little from you for a few months though, just until I sell the thing and make my money. Don't worry though, because it's a sure thing."

"I'll take you over to my bank tomorrow morning and introduce you to the manager. I'm sure he'll be happy to give you a loan on your sure thing. In the meantime, you better get over to Billy's and pick up your load. Unless you don't need a paycheck from me anymore?"

"Jackie, this time it's different. This time I already signed the papers. If I can't come up with the money, I'm in real trouble. You've gotta do this one for me." After I told him that I wasn't interested in his real estate deal, I could see he was really getting nervous. A couple days later my father came over to see me, asking me to help Ray out as a favor to him.

"Yutch, if it doesn't work out the way Ray says it will, you can pay yourself back from the money you and Billy give to your mother each month." This was the first time my father ever acknowledged that Billy and I were still sending him his cut from the furniture wood business we'd started several years before.

"Pop, we're talking $6,000.00 here. If it doesn't work out that will put a serious dent in your lifestyle, yours and mom's."

"I already discussed that with your mother. She's the one sent me over here to see you about doing this for Ray. If you can afford to do this, we'd both appreciate it. Ray needs to get something going for himself financially. He seems to think this real estate thing might work out for him. Your mother and I want to see him bettering himself. You, Annie and Joan, you're all doing well, own your houses, and have dough sitting in the bank. Your brother has nothing. Even his car is hocked to the finance company. Sandy tells us she thinks she's finally pregnant. I don't like coming to you like this with my hat in my hand Yutch, but I'm here, and I'm asking. So what do you say?"

"Sure pop, I'll loan him the money. I hope it works out for him. If it doesn't work out, we'll just chalk it up as a loan that Ray owes to me. I'll get it back when he finally finds his niche in life. I don't want to mess with that other thing with Billy, you and I, because that's working fine, let's just leave it like it is."

"Thanks Yutch, you're all right. I don't care what the rest of the world says about you." So Ray got his money and closed on the deal. Six months later he sold the property for $27,000.00 and I got my loan money back. Ray paid off all his debts and bought a new car and rented a bigger place for him and Sandy and for the baby that was almost ready to be born. He was broke again in a month, and back driving for me part time. The rest of his time he spent looking at properties in the area. He started cultivating married real estate ladies, for his own personal reasons, and in the hopes of making another financial score.

"Jackie, I've found another great deal, and it's absolutely perfect for us. There is a house on a lot and another sixteen acres adjoining it on a separate lot. It's just outside Ledyard, and we can get the whole thing for $9,000.00. We can sell the house for $9,000.00, with just a little work done to it, and have the sixteen acres free and clear." I went out with him to look at the property and thought it was a pretty good deal. By the time we closed on it, we were in the deal just over $10,000.00, and then we spent another thousand getting the place fixed up good enough to sell. Ray took care of anything he could do himself and we got other relatives to handle the rest.

We sold the house for $10,000.00, netting out about $9,000.00 after costs and commissions. We had the sixteen acres free and clear and I was only owed $2,000.00 from the original outlay. Ray sold the land to a builder for $39,000.00, with a down payment of $8,000.00 and a note for another $31,000.00 at six per cent interest per year. We had to be paid off before he could develop the land, no subordination of our interest. He paid us $300.00 a month for about eight months and then got a construction loan and paid off the note. Ray got his half and bought a small house that made Sandy really happy. He bought it from an estate sale and got all the furnishings too. By the time we got our money from that deal, Ray had three other small land purchases that he wanted us to make.He quit driving about then and started looking at real estate full time.

Through Ellen, I found out that Sandy was aware of at least some of Ray's shenanigans with the ladies. Sandy had told Ellen that her father and brothers were the same way, always running around seeing what they could get. Ellen said that Sandy was convinced that all husbands fooled around on their wives when they got the chance. Ellen also mentioned that Sandy felt like sex was an obligation she owed her husband, not necessarily something that the woman was supposed to enjoy doing. I told Ellen that it wasn't any of our business, and that I'd rather not discuss Ray's sexual proclivities. "That's fine with me Jackie. You just make sure that you don't pursue that particular family tradition yourself. I'm not like Sandy in that regard. I expect you to keep it zipped unless you're right here at home with me. Did I tell you that Theresa and I are taking pistol firing lessons over at the sheriff's station every Wednesday night? She's getting to be a lot better at aiming now, but I'm way better than her. I hope you never make it necessary for me to give you a demonstration of my skills with a pistol." I suppose I should have made some protests of innocence about then, but I was too busy wondering about why my dick was shrinking and my balls were trying to withdraw back inside my body. Ellen and my mother are the only two women who were ever able to scare me. Ellen is always serious when she makes a threat. I wish I'd listened to her when she gave me that very direct warning. I blame both my brother and my father for drawing me into that damn family tradition.

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Story tagged with:
Ma/Fa / Consensual / Cheating /