I Won?
Chapter 5

Copyright© 2011 by sourdough

Incest Sex Story: Chapter 5 - John's life goes through some changes when he buys the winning lotto ticket and that's before he's even been paid.

Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Consensual   Humor   Incest   Brother   Sister   Pregnancy  

“I tried to tell them I wasn’t your girlfriend and that I was just your slut, but either they didn’t believe me or they didn’t care.”

“They’re the type who don’t care,” I said. Christ! I win some money and every jerk and his brother is trying to figure out a way to take it away from me.

“I told them I wouldn’t mind getting gang raped if I could choose the gang, but they didn’t think that was funny at all.”

“Some people have no sense of humor.”

“So what do I do?”

“Talk to the school office or call the police?”

“They warned me not to do either or else. I didn’t ask them what the ‘or else’ involved.”

“That figures. Do you know any of these bitches? Their names?”

Elizabeth only knew the name of one of the girls, but she knew all three girls hung out together. She didn’t know if they had any gang affiliations. They wanted the first thousand dollar payment by Friday and then every Friday after that. That gave me a few days to work with, but I didn’t know what the heck I was going to do. I couldn’t go beating them up for threatening Elizabeth. I’d be the one in deep shit if I tried that. I told my friend to plan on going to school tomorrow, but to call me if she felt threatened and I would drive over to the school and pick her up. Once I got off the phone I repeated what I had just been told to Kristina.

“I don’t know what the fuck to do.”

“Maybe I can help,” my sister said.

‘I don’t know how.” She ignored my comment, grabbed her phone and retreated to her bedroom. I couldn’t think of anything useful to do so I logged onto the computer and got on one of the free sex stories sites. I found a couple of stories where there was a lot of killing and maiming of the bad guys. I found myself wishing I had the guts to do the same things this fictional hero was doing to people who annoyed him. It didn’t solve any of my problems, but I did feel a little bit better.

I read porn stories until I heard a knock on the door. I got up to answer it, but Kristina said it was for her so I let her answer it. She opened the door to a tall black girl.

“Jack, I’d like to you meet Fredetta. Fredetta, meet my brother Jack.”

“A pleasure to meet you, Fredetta,” I said as I stood to greet the girl. I was able to look her straight in the eye without looking down. We weighed about the same, but she didn’t look fat. Solidly built like she worked out. I tried hard not to stare at her tits. I felt my loins twitch.

“Nice to meet you too, Jack.” Fredetta had a nice friendly smile. She wasn’t what I would call beautiful, but I had a feeling she knew the effect she had on me.

“Fredetta goes to the same school you recently departed. I know her mom from work. This young lady is going to take care of a couple of problems for us.” Kristina immediately saw the doubtful look I wore and read my mind. She said, “Look, Jack. Those bitches cornered Elizabeth in the girls restroom where a guy can’t go to protect her. Right?”

“Right,” I responded. “I get it now. What about Candy and Mandy? There’s a guy bothering them. Do you think you can handle that problem, too?”

“No need to worry about that,” Fredetta said with a grin. “I’ve been training in mixed martial arts for the past three years. There aren’t that many women in my weight class so I’ve been mainly training with men. There are some men I’ve sparred with who have learned the hard way that I should not be taken for granted.”

“That sounds fine. How much do you want to protect them?”

“Are you talking about money?”

“That’s right.”

“I dunno,” Fredetta responded with a shrug. “My momma told me she needed me to do a favor for a friend so I didn’t expect to get paid for it. I don’t think it will take more than five minutes to put the fear of God into these girls who are bothering your friend or into that guy either for that matter. Will twenty dollars be asking too much?”

“I think my brother can do a little bit better than that,” Kris said.

“He can?”

“How much better was I thinking about, Kris?”

“Your mom told me you will have to interrupt your training at the end of the month until you save up some more money.”

“The school is not cheap. That’s for sure,” Fredetta responded. “Almost 200 dollars a month, but it’s one of the best mixed martial arts schools around here. Any money I can scrape up will be going toward my training. If you can do better than twenty dollars, it will surely be appreciated.”

“Jack was thinking about paying your martial arts school tuition every month for as long as you’re protecting his friends.”

The girl gasped and stared at me like I’d just grown a second head. “You can do that?”

I shrugged my shoulders. “I suppose I can.”

“Who are you, that lotto winner?” I nodded my head. Fredetta grinned and took me by surprise when she wrapped her arms around me. “Nobody’s gonna lay a hand on any of your women unless it’s you, you hear?”

“I’m glad to hear you say that.”

“I heard about that fight. I’d be happy to deal with that clown for you, too. No extra charge.”

“Thanks for the offer. I think I proved I can handle him by myself.”

“You do realize he’ll most likely have help the next time, don’t you?”

“I don’t doubt it.” I already knew that when he showed up at the biker bar with friends.

“Okay. Let me know. One last question,” Fredetta said. “Are you in the market for another girlfriend for your harem?”


“I’m still a virgin, but I’m a quick learner and eager to please.” The young woman gave me a sultry smile and nudged her pelvis against mine. Mr. Stiffy responded like a champ and was already wanting to come out and play. I could hear my sister giggling.

“He’s kind of shy, Fredetta,” Kris said. “You’ll probably have to seduce him like the others did.”

“I am not shy,” I protested. “And I was not seduced. It’s just maybe we can talk about it? After some of this settles down?” I didn’t want Fredetta to feel like she’d been rejected so I gave her a pelvic nudge of my own so she could feel my stiff dick poking her. She smiled in return.

“Whenever you’re ready,” Fredetta responded. We exchanged phone numbers and she told me to have the girls contact her tonight so they could arrange to meet them at school before classes tomorrow.

“Phew!” I exclaimed when my newly hired muscle left. “I guess I don’t have any self control.”

“Oh, I think you used remarkable self control.”

“What do you mean, Kris? I wanted to fuck Fredetta just like I’ve wanted to fuck practically every girl I’ve met lately.”

My sister giggled. “Not that she didn’t want you to. She was begging for it, but you were a gentleman. That’s what I call self control.”

“I can tell I’m not going to get any sympathy from you.”

“You don’t need any sympathy from me, Jack,” Kristina responded. “Listen. You just won a shitload of money and you have girls and older women falling all over you. No great surprise there. Sure. Money and women bring along their share of problems, but it beats poverty and beating off alone in your bed each night. I don’t think there is anything you can’t handle so don’t start feeling sorry for yourself.”

“I’m not feeling sorry for myself,” I protested. “I just think I won’t be to do right by any of these women if I have too many of them.”

“Oh my!” Kristina exclaimed. “What a problem to have. You poor boy. As far as Fredetta is concerned I don’t think you can go wrong. In fact, you’ve been very lucky with all the women you’ve gathered so far. And believe me when I tell you that you’ll hear it first from me if I feel any woman you meet isn’t right for you. As far as doing right by your women I think you’re doing fine so far.”

“I am?”

“Sure you are. Look. What these women are looking for is a feeling of safety and security for themselves and their children. Cynthia, Sandy and I tried to find it by marrying a man. Well, you know how that worked out for me with Rick. The younger girls are looking for the same thing as their mothers. Each one has a faint hope that she will be the one you will marry.”

“I know they all want safety and security.”

“That’s right,” Kristina said. “I don’t see any of those women as gold diggers or fortune hunters. If I find out otherwise, I’ll be showing her or them the door, forcefully if I have to.”

My sister finally convinced me I was in fact doing right by these girls and I shouldn’t worry about how I was treating them. But she did say that she was gong to put me under close surveillance from now on so I didn’t pick up any future strays. Kristina also told me she was gong to be busy for the next couple of weeks with appointments for Jackie and herself and would be using the car.

“It’s your car,” I pointed out. “So you can do anything you want with it.”

“I know,” my sister responded with a big grin. “I’m still not used to that fact yet and it’s nice to be reassured.” I didn’t feel the need to buy a car for myself right away, but it was a nice feeling that I could when I wanted to.

Fredetta must have done something right. Less than 48 hours later Elizabeth called and told me the three girls who had been threatening her for cash were now acting deathly afraid of her. Then Sandy reported that the guy who had been bothering Candy and Mandy came to school with his arm in a sling and and acting totally uninterested in her daughters. He claimed he slipped and fell and was looking into suing the building owner where he fell. I called Fredetta’s martial arts school and arranged to pay the next 12 month’s tuition. They gave me a one month discount for paying Fredetta’s tuition a year ahead. Kristina reported that Rick had been served with divorce papers. Tom Paine called me and said my lotto money had been deposited. I was rich. He also sent me a bill. Man! The guy wasn’t working on the cheap. Still, I felt good paying him. He was protecting my interests.

“Mr. John Dempsey?” The man asking was standing outside the school district building where I took my exams.

“That’s me,” I said.

The man handed me a packet of papers and said, “You’ve been served.” I was bewildered more than anything else.

“Uh, thanks.”

“You’re welcome,” he replied with a surprised look and left. I guess he wasn’t used to being thanked.

A quick look at the top paper told me what I needed to know. Rick was suing me for fraud, misrepresentation, breach of contract and a bunch of other stuff. Some of the allegations were a complete mystery to me, but the long and the short of it told me that he wanted all of my lotto winnings. It was no surprise Rick had found me. I wasn’t exactly in hiding. It didn’t take long for me to complete the exam I had come to take. I put in a call to Tom. He was in court so I told his secretary that I had been served with a civil complaint. She told me to get a copy of the complaint to Tom’s office and asked who was representing the plaintiff. I recognized the lawyer’s name. He was the same guy who represented Rick on that drug plea bargain. I guess you go with who you know. I found an Office Depot and faxed the papers to Tom’s office. Tom called me later that afternoon.

“I made a courtesy call to the plaintiff’s attorney,” Tom said. “I told him that my firm is representing you and we would be responding to his client’s suit. I also asked him to direct further communications to my office.”

“What did he say?”

“About what I expected. He claims to have an excellent case and the evidence will show that you cheated your brother in law out of the winning lotto ticket that rightfully belonged to him.”

“That’s total bull.”

“You know it. I know it. I’m certain Rick and his attorney know it.”

“So what’s the point?”

“I got the impression that they would rather settle the case in an expeditious manner instead of letting the case drag on for years,” Tom said. “In fact, the plaintiff’s attorney told me he was authorized to negotiate a settlement on his client’s behalf immediately. I told him I wasn’t authorized to negotiate anything on your behalf, but I would relay any settlement offers to you for your consideration.”

“So in other words, Rick wants me to give him some money. In return he’ll go away and stop bothering me.”

“That’s correct.”

“How much money?”

“He suggested half of your lotto winnings would be a fair settlement of the case. I suspect they would settle for a lot less.”

“Tell them to go stick it, Tom,” I responded. “We’ll see them in court. And don’t listen to any more settlement offers. I don’t want Rick to get a single dime of my money.” We spent a couple of minutes discussing some other matters. I wanted Tom to draw up a will and set up a trust fund so that my family would be protected if anything happened to me. Jeez! I thought. I’m 18 years old and I already have to start thinking about my eventual death. I hoped it was a lot later than sooner. Tom referred me to a CPA and an investment adviser. I promised to make appointments with both outfits and we ended the call.

“Do you want me to talk to this Rick person,” Fredetta asked.

“No, thanks,” I said. “I have a feeling you ‘talking’ to that clown would create more problems rather than solving any existing ones. Thanks for the offer though. I may take you take you up on the offer at a later date.”

“Any time,” my latest bed partner said. Fredetta had shown up at my door not too long before that phone call.

“Which one is your bedroom, Jack” she demanded.

“His is the one on the left,” Kris said.

“Uh, what’s this about?”

“No one pays a year’s worth of my tuition without getting something in return. You’re getting my cherry right now.” The tall black woman grabbed my hand and pulled me toward my bedroom.

“You don’t have to do this,” I protested. “You deserved that tuition payment after the way you protected the girls.” Fredetta ignored my protests. I resisted a bit, but not too hard. I didn’t want Fredetta to think I didn’t want her. I did want her. The bedroom door closed behind us and we both started ripping our clothes off without a further word exchanged. I could tell the young woman was getting kind of shy when she was finally naked standing before me, unsure where to place her hands. Not nearly as self confident as she was acting a few minutes before. I decided I didn’t want a frantic fuck. I climbed onto the bed and motioned Fredetta to join me. We embraced and kissed.

“Are you on the pill,” I asked. “You won’t be be able to continue training if you wind up carrying my baby. Also, you have to ask yourself; will a pregnant bodyguard ever be taken seriously?”

“Thank you for asking,” Fredetta replied with a giggle. “I don’t believe any other man who would have bothered to ask and I appreciate your concern. To answer your question: yes, I am on the pill and have been since I was 12 years old. That was when older boys and men started badgering me for sex. The very real fear of being raped was what prompted me to start studying martial arts. To earn my tuition I became a babysitting demon.”

“You can probably start cutting back on your babysitting jobs,” I said.

“That’s for sure,” the black coed replied and followed that up with a kiss. “Now, are we going to continue talking or are we going to get down to some fucking? I hope it’s some fucking because I’m anxious to find out what a man’s dick feels like inside my pussy.”

“I’m ready whenever you are,” I responded. Fredetta straddled me cowgirl style, lined up my prick with her pussy and sat back spearing herself in the process taking me by surprise. That had to hurt I thought as I saw her flinch.

“Are you all right?”

“I’m fine. It did sting a bit though.”

“No sense in hurting yourself. Take it easy. We’re not in any rush.”

“I’ll be all right,” Fredetta said and started moving. Slowly and tentatively. Her eyes were closed and she seemed to be concentrating. I didn’t move and let the girl set her own pace. Gradually she picked up her pace and smiled. “Oh, I like this!”

“I was hoping you’d say that.”

Fredetta closed her eyes again and began to hum tunelessly as she rocked back and forth on my dick. I concentrated on my own feelings and admiring the girl’s perfectly fit body. My own pale hide appeared sickly beside my new friend’s dark brown toned skin. I resolved to start working on my tan as soon as possible. My first interracial experience, I realized. A child born to us would definitely have darker skin than me. The thought of fathering a biracial baby made my loins twitch and I started returning the black girl’s pelvic thrusts with thrusts of my own.

“Fuck me faster, fucker. I’m getting all shuddery.”

“I’m fucking as fast as I can,” I growled. I pulled the girl down against my chest and thrust harder finally emptying my sperm inside her.

Fredetta kissed me and said, “My finger used to offer the best sex I knew about before this. Now, it will have to take a back seat to your dick.”

“I hope your finger doesn’t get jealous.”

“My finger won’t get jealous as long as I keep using her. And I’m going to be using her plenty, but I’ll be thinking about you and your dick while I do it.”

“Aw, that’s sweet,” I said and kissed her. “Are you ready to go a second round?” That’s when my phone rang and I saw it was Tom. My second round of fucking with Fredetta was much more leisurely.

“Well, that was a surprise,” I told Kristina after Fredetta left.

“A pleasant surprise, I hope?”


“Good,” my sister responded. “I knew you’d be pleased.”

“You knew she was coming?”

“Of course I knew. I arranged for Fredetta to be here.”

“Why didn’t you tell me?”

“Then it wouldn’t have been a surprise.”

I shrugged my shoulders. “I guess that makes sense.”

“It makes perfect sense,” Kris said. “No guessing about it.”

“From now on, will you please tell me when you plan on having one of the girls over?”

“That’s no fun. There are no surprises then.”

“Just the same, I would appreciate a little notice.” Actually, I would have preferred making my own dates, but it looked like Kris was having a lot of fun and I didn’t want to spoil it for her too soon.

“If you want it that way,” my sister said. “Then I should tell you that tomorrow about this same time, Candy and Mandy will be here for a threesome with you. The day after that is Sandy’s turn. She told me you want to do anal with her so she purchased some K-Y Jelly and has scheduled an enema so that it won’t be so messy for you and uncomfortable for her. Elizabeth, Cynthia and Carol each want an overnight alone with you so they’re scheduled in that order for the following three nights. After that we start the same rotation all over again until I get the okay from my doctor to start fucking again. Then I’ll schedule myself into the rotation. Of course, there are some unknowns like if Mom wants in when she gets back from deployment or if you meet someone new who you want to add to the harem. Any questions?”

“Do I have any discretion about who I want to see and when I want to see her?”

“Of course you do,” Kris responded. “You can call all of them right this very minute and tell them that you’ll be the one to decide who you want to see and when you want to see her. You can also tell them not to listen to anything I say from now on. They’ll all be agreeable to that. At least they say they will. But then be prepared for a lot of whining, complaining, wheedling and begging from the women wanting more of your time than you’re willing to give them.”

Hmm, maybe she had a point. “I didn’t think of that.”

“That’s obvious. I’m training them to go through me if they want to see you. Sort of like a gatekeeper.”

“I get it now,” I said. “Good idea. Okay, you can be my gatekeeper to keep the girls in line.”

“Actually, I was thinking of myself as your pimp.”



“Okay fine. You’re my pimp.” I gave my sister a hug and a kiss. “Thanks for watching out for me, pimp mommy.”

“You’re welcome.”

The next day I opened up accounts with the investment and accounting firms Tom recommended. I was warned about gifts like the car I purchased for Cynthia. The value of the car would be counted as income for her and I would be liable for any additional taxes. Oops! That was good to know. I stopped at the bank and put Kris on the account with me. I didn’t want her to have to go to me every time she needed money.

“I appreciate that,” Kris said when I told her what I did. “But let’s keep quiet about it for now. I don’t want Rick demanding spousal support if he thinks I have access to any of your money.” Good idea.

Sex with Candy and Mandy was fantastic except it seemed like the little demons were trying to fuck me to death. By the next morning I decided I wasn’t going to have both in bed with me at the same time. I just wasn’t man enough. Sex with Sandy was just as intense as it was with her twin daughters. I guessed their talent for fucking ran in the family. I chickened out doing anal with the older lady. I knew I wasn’t going to do anal with anyone ever and I was going to stop teasing the girls about it.

Afterwards, Sandy whipped up dinner for us. It was delicious. Better than anything I’ve ever tasted. Kris and I looked at each other and I think we both had the same idea.

Kris said, “Um, Sandy? Would you consider cooking for Jack and I on a regular basis?”

“I would love to cook for you two,” Sandy responded. “But I don’t see how I could do that on a regular basis with my two jobs.”

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