Billy Sings The Blues

by Openbook

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

Desc: Sex Story: The Sixteenth story in the Caddymaster Saga. Billy gets Jackie involved in straightening out his mess. Theresa decides she has a way to slow Billy down in a hurry.

Chapter 1

Billy and I had just finished having our final business meeting and discussion with my father. It hadn't gone well for any of us. It ended up with him paying us a dollar for the Mustang and telling us to stick the rest of his share of the business up our asses. We had all known that it wasn't going to turn out that well when he had shown up drunk, for an eleven o'clock morning meeting with us.

In a nutshell, he had taken to treating all of his friends and acquaintances to drinks and lunches and charging it to the business. Billy and I had finally had all of that we could take and had deducted $1,404.45 from his third of the profits for the past month, and presented him with a bill for the remaining $644.03 in disallowed expenses. We told him that we wouldn't pay anymore for his boozing it up with his buddies. Mostly, it was the money, but part of it was our fear that he was going to kill himself or someone else with his drinking and driving in a company car. My mother had been after me for months telling me that the drinking would kill him if he kept it up.

"Jesus, Jackie, that was rough. I hope your dad understands we didn't want it to end like that."

"Billy it wouldn't matter how we did it, it was always going to end up like this sooner or later. If we'd continued letting him stick all his boozing costs on us, he'd just have kept increasing it until there wasn't any money left for anybody. That's just how he works. He won't stay inside reasonable limits and restrictions. Those are for 'normal' people, not for someone like him. Nobody can tell him what to do or how to do it. I don't know how he managed to get his 20 years in in the Navy, but he did. His buddies always protected him is all I can figure, because he was like this in the Navy too."

"If it wasn't for him, we wouldn't have made the kind of dough where he could drink up that kind of money every month. I hate to just kiss off the money he was making for all of us. Maybe we should let him sober up and cool off and try to work something out with him."

"You can do that if you want to Billy, but I want no more part of him running around in a company car drunk on his ass. He gets in an accident, we lose everything. I'm talking this farm, my house, both our businesses, any money we might have saved. Every time he gets in a car in the shape he's in now, that's a real possibility. Maybe you're willing to risk having to start over from scratch, but I'm not."

"You going to just walk completely away from the business? There's still good money to be made there."

"No, I'm not saying that we walk away from anything. He already had every wood maker in a hundred miles knowing about us and what we could do. We can see to it that they are kept up on what we charge for the wood that they need. Most of our business is just repeat business anyway. I bet he hasn't talked to anybody new in three months, and hasn't seen any of his customers, unless they ran into him in a bar by accident, in just as long. As long as they keep calling in their orders, we keep the business going. Dad gets his third just like usual, but we'll give the money to my mother, not to him. She won't let him piss it all away on his friends, and she won't let him get so out of control with his own drinking. She's used to keeping him on a short leash where drinking money's concerned."

"That's good, Jackie. This way he gets some money plus we keep getting ours too. Without his expense account money to worry about, we'll be doing better than ever. That's why I like keeping you around. You can always find a way around the problems."

So that's exactly what we did, and Billy was right, we were doing better than ever before without all the expenses of going out and getting new business. Business fell off some as people had businesses go under or they found other suppliers, but it was good for a long time. We even got new customers from time to time, when our regular customers gave good recommendations to new businesses that needed wood. We had a quarter page ad in the yellow pages that brought in some business too.

My father was yakked at Billy and I for a couple months until he saw that we were bringing his share over and giving it to my mother. He never acknowledged that we were doing it, but we all knew that he knew about it. He didn't have the business to use as an excuse to be out 'ramming the roads' as my mother referred to it, and so he spent more time at home and settled back to a slower, but still steady, drinking style. At home, my mother mixed his drinks, and she would water them down quite a lot when she felt he had indulged enough. Her system must have been pretty good, as he lived to be eighty one. If she hadn't died eight years before him, he might have made it to one hundred.

It was about three months after that meeting where dad quit the business that Ellen got a phone call from a crying and distraught Theresa. She claimed that Billy was seeing another woman and she asked Ellen to speak with me, and to try to get me to have a talk with Billy and straighten him out. Billy and Theresa had three kids at that time and the youngest was still in her diapers. Ellen spoke with me, but I told her that I knew nothing about Billy seeing anyone else and told her that I didn't see how he could have either the time or the energy with everything he had going on. Of course, Ellen figured I was just covering up for Billy and began suspecting I might have something going on the side myself. I asked her how Theresa knew about this other woman if there was one. Ellen said that Theresa had a strong feeling and that women knew about things like that. Sounded like bullshit to me, but I told her I'd check into it anyway.

We were out in the front at the farm, Billy was loading up my truck for a firewood delivery over to Stonington. I asked Billy if he was up to something, like seeing another woman or something. He just looked at me and then told me no. I dropped it without another word and we talked about a new job he'd bid on and felt like he'd probably get it.

"Why'd you ask me something like that anyway, Cuz? Have you got a guilty conscience yourself or something?"

"Billy you just looked sneakier than usual, that's all. I figured you were up to something and I was hoping it wasn't anything that could really get your ass in a sling. Because, if you were fooling around, well Theresa would know it, and probably right away too. I'd hate to see you fuck up everything just for some strange piece of ass."

"You hear anything like that Cuz? Rumors or something?"

"Maybe I heard Ellen on the phone yesterday talking about somebody screwing around on their wife, but I didn't get a name. It couldn't be you though, because you already said it wasn't." Billy walked around to the back of my truck where he couldn't be seen from his house. I followed him back there. He had his bandanna out and was wiping the sweat from his face and neck.

"Jackie, please don't play with me. Tell me what you heard, please?" Not all that sweat was from working, I guessed. He looked worried.

"Billy, Theresa called Ellen. She's suspicious I think. She has a feeling or something. I don't know what you might really be up to, but I'd quit it if I was you."

"I can't quit it, she's having my baby. It's driving me crazy, Jackie, I don't know what the fuck to do. You're good at figuring shit out, what can I do?"

"Goddamn it! Don't you have enough shit on your plate already? Why in the name of Christ would you do anything so stupid? Did you think Theresa wasn't going to notice you pushing some other woman's baby stroller? Who the hell is this other woman anyway?"

"You don't know her. I met her down at the hall of records when I was pulling some permits to do the Pearson farm last year. She works there and was helpful to me. After I had everything filed and the permit in my hands, I asked her out to lunch, to let her know that I appreciated her help and all. We didn't do anything right away, just talked and went to lunch a few times that's all."

"If she's having your baby, then I guess you must have fed her your salami at one of those lunches. You don't get pregnant from eating lunches, fat maybe, but not pregnant."

"Yeah, after awhile we had our lunches in her apartment. She didn't want people to get the wrong idea about us having so many lunches in public together. I told her I was married and everything. We were having one of those lunches when afterwards we started kissing and fooling around. It kind of got a little out of hand that's all. Now she's pregnant and I don't know what to do."

"Are you saying this only happened the one time and she got pregnant from that time?"

"No, we've been seeing each other a couple times a week for the past seven or eight months now. She's three months pregnant now."

"Billy, tell me her name and give me her address. What would you like to have happen here?"

"I really like her a lot Jackie, but I love Theresa and the kids. I wish she wasn't pregnant, but I like her and I was happy going off to see her once in awhile. I don't want to lose Theresa. I don't want her to ever know for sure. It's killing me now that you told me she suspects something."

Billy gave me all the information he felt I needed. He was so worked up that I had to tell him to calm down and try to act natural. I told him I'd try to think of some way out of it for him, but I made him promise to stick close to home until I came up with something. I drove over to Stonington and made my delivery and then drove home. I was trying to think of something I could do to help Billy and also Theresa. She didn't need this from him and I knew she'd take it bad if she found out. Finally I decided that I had to get Ellen in on it too. I figured Ellen could do some investigating and find out more about Billy's girlfriend, like she had done with Joan in their assault on B.D. Poynton. Her mind was more devious than mine, and she could be colder and more calculating than I could. I thought about bringing in my mother too, but that would have been overkill.

"Your telling me that Billy admits to getting some poor girl pregnant and cheating on his wife, and you think I should try to help him out? Why would I want to do that?"

"I think it would be more like helping both Billy and Theresa and their kids. If all I wanted to do was help Billy, I'd be able to do that by myself."


"I'd go have a talk with the girl and pay her some money to leave Billy alone. I'd have her sign a legal paper that was enforceable in court and sue her ass if she didn't live up to her end."

"So why didn't you just do that then?"

"Because Billy would just go out and do the same kind of thing with another girl. He wants to keep this one if she isn't pregnant any more."

"What do you think I could do to help Theresa and not encourage Billy to keep doing it with someone else?"

"First, we need some more information about this girl. I thought you'd be great at making friends with her and finding out more about what she's like. If she's a nice girl, it might be hard to work something out. She knows Billy's married and went ahead and let him get her pregnant anyway. I'm guessing she isn't exactly as pure as the driven snow. See if you can learn something in the next week or so." I could tell that Ellen was excited about having a chance to do some role playing, so I just left her alone with all the information I'd gotten from Billy.

Our plan might have borne early fruit if Billy hadn't gone inside his house ten minutes after I left him and confessed everything to Theresa. Billy wound up living back on Bill Avenue with his mother, and Theresa was on the phone with Ellen almost every waking moment for the next week. Billy could go to the farm to do his work and that was it. Theresa wouldn't talk to him and wouldn't let him in to see his children. She told him that she'd divorce him right away if he tried to speak with her again before she figured out for sure what she was going to do.

She wouldn't even let Billy inside the house to take orders for wood or to schedule deliveries. We ended up having to get a phone installed outside on the porch. We had to get a special loud ringer put in so that Billy could hear the phone from wherever he was on the property. I told Billy the costs were all coming out of his end.

Ellen went ahead and spent some time finding out about Amanda Lawrence and even managed to have herself introduced to her by one of her co-workers. She had been born and raised in New London and had been working for the county since graduating high school in 1962. Ellen said she was cute, in a brassy kind of way and had a nicer figure than Theresa, even pregnant, which Ellen said she wasn't showing yet. The people she talked with didn't know about Billy and her, let alone other men in her life. Ellen didn't think she'd get anything else useful because Amanda wasn't very sociable.

I decided I had better get my brother Ray involved. Ray was practically engaged to Sandy by then, but he was always willing to help a family member out if there was a pretty girl connected somehow with his helping. Ray figured it would be better if Sandy wasn't aware of just what it was that he was doing to help the family and made Ellen and I promise not to tell her. Two days later, a little before six in the afternoon, he was back with his report.

"Jackie, that girl's not pregnant. At least she's not pregnant right now."

"How do you know that, Ray, did you just come out and ask her?"

"Well, last night she was wearing a Kotex, and it had fresh blood on it. I saw it and I could smell it too. I can guarantee you that she isn't pregnant right now."

"What did you do, go through her trash can?"

"No, of course not. She was wearing it when I checked."

"This is important Ray, are you sure? Don't make shit up to try and look like some great cocksman. This is too important for any bullshit."

"Jackie, I'm telling you. I was on her sofa last night at 9:30 and had my hand right on her panties and I felt the Kotex and the belt. I took a peek later and made sure she needed it, and she did. She thinks I'm coming over again tonight, but I'm not. I hope you're going to reimburse me for my out of pocket here because I blew almost twenty bucks on dinner and drinks and some gas for my car." I got a pretty good blow job out of it so I won't charge you for my time." I gave him the twenty and thanked him for his quick attention to the matter, his detailed report, and the dedication he showed to the family. "Always glad to give you guys a hand, you know that."

After he left, I told Ellen about everything Ray had told me. She seemed more concerned that Ray would step out and cheat on Sandy than she was about the news that this Amanda was running some kind of scam on Billy. I tried explaining to her that Ray had only been doing what we sent him over there to do. I think it was the blow job that bothered her the most. I started being afraid that Ellen might say something to Sandy about Ray's behavior, but she didn't, or at least I never heard anymore about it.

It took Ellen less than five minutes to get on the phone with Theresa and tell her that Billy wasn't fathering a child with Amanda. You'd think she'd be happy finding that out, seeing as how it made the whole situation less complex and all. Not Theresa though.; If anything, she got even more pissed off that Billy would be so easily duped by another woman. By the time she and Ellen got off the phone, Ellen was worried enough about what she'd been told that she told me to find Billy and make sure he stayed away from the farm for awhile. She didn't tell me why, but I could see she was worried and upset. I called Billy over at Aunt Margaret's and told him I'd be over there to pick him up in half an hour.

After I picked Billy up, we went down to the bowling alley and bowled some candlepins. I lost ten bucks to Billy, but I managed to get him to repay me for the twenty I gave to Ray. Billy was pissed when I gave him Ray's report. He didn't like Ray getting a blow job from his girlfriend. I asked him if he was stupid or just couldn't see the trouble he was in.

"Jackie, would you like it if he got your girlfriend to suck his dick?"

"That's not the point here Billy, I'm married, I don't have a girlfriend to suck his dick. I wouldn't want one who'd suck his dick either, but that's besides the point. The point you should be worrying about is that Amanda's not pregnant. a secondary point is that she went out on one date with Ray and wound up sucking his dick and letting him play with her bloody pussy. That isn't painting too nice a picture about the way she views the relationship you and she have. If it was me, I'd start having second thoughts about whether to continue your little affair with her. Another thing, Ellen already called Theresa and told her about Ray and Amanda and Theresa said something that has Ellen scared, but I don't know what it was. Ellen told me to make sure you stay away from the farm for a few days at least."

"I'm glad she isn't pregnant Jackie, but I'm still not happy about Ray's finding out the way he did. As for staying away, that's my fucking farm, not Theresa's. I had that farm before she and I got back together. It's in my name, and she's only there because I'm letting her stay there." I knew right then that there was nothing more I could do other than step out of his way and let happen whatever was going to happen.

Billy was as stubborn and intractable as my father and I were. None of us were known for being reasonable or controllable even under the best of circumstances. Add emotion to the equation and 'powder-keg' would be a more apt description for any of the three of us. I drove him back to my aunt's house and went home. After I told Ellen that I was done with the whole thing, and told her some of what Billy had said, she just nodded to me and said nothing.

The next morning at about six o'clock, Theresa emptied a six shot revolver into Billy as he stood on their front porch steps. She wasn't much of an aim though, managing only two hits in six attempts from less than ten feet away, but she did convince him to stay away from her and the children for awhile. Billy drove himself to the hospital and called my father before letting them operate to take out the bullet in his thigh. The other bullet had passed right through his other thigh. My father told Billy to just keep his mouth shut about how it had happened, and then he got Mr. Bennett on the telephone and arranged to meet him at the hospital. My mother called me about seven thirty that morning to tell me the news. Ellen and I drove over to the farm to see what we could do for Theresa. By the time we got there, Big Tony and Maria were there taking care of the kids and trying to get Theresa to stop crying.

At about ten that morning my father and Mr. Bennett drove up with a guy from the state police and picked up the revolver that Billy had 'accidentally' set off when he dropped it that morning. I'm not sure how they came up with an explanation of how Billy managed to shoot himself twice with a single drop of a revolver, but they must have come up with something, because it was ruled an accidental shooting and Billy even got his gun back after a couple months.

I finally left Ellen with Theresa and the mob that had come over to see what was up, and went over to the hospital to see Billy. They had him on some kind of medication for the pain and from the surgery, but he was awake and wanted to know how Theresa was. "She was aiming for my crotch you know, trying to put me out of commission as far as the ladies go. The first shot she got me in the leg where they operated, and then I was trying to move and duck away from her and jump off the damn porch. She was pretty damn mad too, when she saw me limping over to my truck. I didn't even know about the other wound until I looked down on the drive to the hospital and saw the blood on the other leg and the hole in my pants. My truck is all full of blood Jackie. Could you take it somewhere and get it cleaned before the stains get all dried up and I can't ever get them out?"

"Billy did you learn anything from this morning? She could have killed you and then she'd go to prison and who would raise your kids then? Tony and Maria? Is that what you want? You can clean your own damn truck too, when they let you out of here. I told you last night to stay away for a few days and let her cool off, but you had to do it your way. I'll stop by and see you tomorrow, just to see if you need something. You know the business will get all fucked up with nobody to answer the phones now."

I got his keys and went out and took his truck back to the farm and washed it out as good as I could. There was still a stain, but not too bad, and the smell was pretty much gone too.

I told Theresa that the first thing Billy wanted to know was whether she was okay. Then I told her that the doctor had sewed his dick back together but didn't think he'd ever be able to use it again. I was smiling as I said it to make sure she knew I was only kidding with her, but she looked nervous when I'd said it. Maybe Billy wasn't quite as bad in bed as she'd led me to believe so many years before.

Ellen and I took Billy's truck back to the hospital and then got in my car and drove home.

"How was Billy taking things, is he pissed off?"

"I don't think so. He sounded kind of proud actually. Billy always did appreciate brute force and violence. I think that's why he admires my dad so much. He's happy he got off as easy as he did, because he knew she was trying to shoot him each time she pulled that trigger. He was more worried about the bloodstains on his truck seat than about his leg wounds or his close call."

"You know, almost all the men in your family are a little crazy. You don't think about things the same as most people. Anybody else gets shot, they lay down and bleed to death. I'm surprised Billy didn't run into the house while Theresa was reloading the gun and get himself a towel to protect his truck seat from the stains. I'm glad he's going to be okay this time, but don't be too surprised if Theresa finishes the job when he gets out of the hospital. She's still very angry with him."

"Okay, I won't be surprised. Don't you be surprised if she visits him in the hospital every day and them takes him back and nurses him until he's all better. We may be crazy in my family, but we always seem to marry women who stick with us no matter what."

"Don't kid yourself that I'm that kind of woman, Jackie. And I'm pretty sure I'm a better shot than Theresa."

"You'd almost have to be a better shot than her. It happens though that I never would do anything to give you cause to shoot me. That Amanda is more Ray's, Billy's and my father's type. I prefer tall, skinny girls with dirty minds and active imaginations."

"You really think I'm skinny?"

"I wasn't talking about you."

"Can I get a gun Jackie, please?"

"Over my dead body."


Chapter 2

Ellen and I drove over to New London a few days later and brought Billy back home with us. I'd been over at the farm trying to take care of as much business for Billy as I could, but hadn't really been able to keep up with everything that needed doing. I didn't know anything about the logging portion of his business, and had to rely on the men who'd been working for Billy the longest. Theresa seemed to have gotten herself mad at me as well, doing whatever she could to keep me from working effectively at the farm. It looked like she was probably thinking that she needed to punish me too since it appeared like I was on Billy's side about everything.

"Teri, Billy's my cousin and he's also my business partner. While you may be perfectly willing to see everything we've worked for come crashing down around our ears, I'm not. I didn't talk or encourage Billy into deceiving you, and I'm just over here trying to keep our work shit together so that both our families can keep putting food on the table. You can be mad at Billy and shoot his ass all you want to, but quit trying to make it difficult for me to try and keep everything somewhat together."

"Billy told me that you told him to not tell me about his girlfriend. You knew about it and should have stopped him."

"How was I supposed to stop him, I only found out about it ten minutes before he told you about it himself? I told him to knock it off, as soon as I found out, and I was trying to get it stopped at the other end when you decided to unload your pistol into his pants. I don't understand how you could do something like that? You could have killed him, and then where'd you be? In the women's prison that's where! How about your kids then? You want your mom and Big Tony raising those kids of yours while you sit in a cell for the rest of your life? You can't just act on your emotions, Teri, there's too much at stake for everybody."

"You keep him away from here and I won't shoot him again."

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Story tagged with:
Ma/Fa / Consensual / Cheating / Oral Sex / Pregnancy /