What if You Won the Lottery Ch. 01

Keeping it all in the family, Mark has incestuous sex with his mother, his sister, his aunt, his cousin, and his grandmother.

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Note: This is a true story as told to me by Mark for me to write for him.

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Think about it, what would you do if you won the lottery jackpot? Don't answer yet. Think more about it. Imagine all of the things you could do, the places you could go, and the things you could buy. Now, what would you do if you won the lottery jackpot?

What if you won enough money that you could practically do whatever you wanted to do and whenever you wanted to do it. Where would you go if you could go anywhere in the country and/or in the world at any time you wanted to go? I'm sure over the years, you've already given it some thought. So, think about it again now. Where would you go if you could go anywhere? Where would you live if you could live anywhere?

"So, tell me, what would you do, where would you go, and where would you live if you won the lottery jackpot?"

There are two things in my life that I thought would never happen. Winning the lottery was one of them, and satisfying my every, sexual desire was the other. Yet, after winning the lottery, I not only had all the money that I'd ever need but also, I was able to make my every sexual fantasy come true. With just one lottery jackpot win, I satisfied my every materialistic need and my every sexual desire.

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Ever since I turned 18-years-old, believing that I'd win, I faithfully played the lottery every week for the past six years. Not much of a gambler, I played one, two-dollar ticket a week, every week, I played the same numbers, my birthday, my mother's birthday, and my apartment number. It was worth the two-dollars to dream of all the things that I do, all the places I'd go, and all the things that I'd buy if won. It was exciting to check the winning number the next day to see if I won any money.

Disappointingly, I never won more than a free ticket. Most times, I didn't win anything. Most times, I didn't even match one number. I thought about giving up and not playing the lottery, yet, if I don't play, I can't win. Besides, it was only a lousy two-dollars, a lousy two-dollars that could change my life. If I smoked or drank, I'd spend much more than that on cigarettes and beer every day.

Then, I had a thought. Instead of playing the same numbers that I played every week, I had the lottery machine pick my random number to play. I played a quick pick and played quick pick numbers every drawing thereafter, until I returned to playing my old number and a quick pick number. Now, instead of spending two-dollars a week, I spent four-dollars a week.

Then, during one drawing, it happened. When I checked my number the next day, I couldn't believe it. I won. I won on the quick pick ticket. I won the $320-million-dollar jackpot. Doing some quick mathematical computations, taking the one-time payout, before taxes, I estimated that my cash winnings were around $213-million-dollars and 138-million after federal taxes. Not bad for a four-dollar wager.

Not as much as I could do with 320-million-dollars but there was still a lot that I could do with $138-million-dollars. Not rushing out to spend money helter-skelter, I needed to give it a some thought and a lot of financial planning. First things first, I needed to hire a financial planner to help guide me on how to invest my money and to make it grow.

Yet, realistically, I knew that I'd be spending a good portion of the money in short order. Instead of renting, I'd buy a house, a big house somewhere nice and safe, and somewhere no one knew that I won the lottery. Having no idea where I wanted to live, I hired a real estate consultant to help me find my perfect home.

Someplace out of the way and away from the fray, she helped me decide on Vermont. I've always loved the drive to Vermont, so fresh, so clean, and so scenic. Sometimes during my drive, I didn't see another car. Actually, no exaggeration, I saw more cows than I saw people.

Now, that I knew where I was going to live, I needed to find a house. I'd want a house with at least five bedrooms on an acre of land with an in-ground pool. I'd fill the house with comfortable furniture, an oversized, leather couch, and matching leather reclining chairs to start.

I bought a house with six bedrooms, five acres of land on a private road, and in inside, four, season pool. The heated pool was a luxurious, Godsend during the winter. Peacefully quiet, the scenery was picturesque as if from a post card. With this God's country, I couldn't imagine any place better to live.

I bought a comfortable, king-sized bed and a big screen TV, one for downstairs and one for upstairs. Leaving the other three bedrooms unfilled until later, I bought two more king-sized beds for guests. With me not married and not even having a girlfriend, I didn't want to unnecessarily fill my house with stuff that I wouldn't use and didn't yet need. Once I found my special someone to fill my life, I could always buy what I needed and all that she wanted later.

I'd buy a couple of bad ass cars. Already knowing the cars that I want to own, I'd buy a Shelby GT 500 with all the options, at around seventy-thousand-dollars. Another car that I always admired and wanted, I'd buy a Bentley Continental GT coupe, the one with the V8 instead of the 12-cylinder engine, around two-hundred-twenty-five-thousand-dollars. Then, for those days when I'm snowed in, I'd bought a one-hundred-thousand-dollar Range Rover. No matter how much snow I'd get, those things never get stuck in the snow.

Between the house, the furniture, and the cars, having plenty of money left over, I figured that I spent a little more than three-million-dollars.

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High on my bucket list of things to do, I could retire. I could travel wherever and whenever I wanted. Something that I always wanted, I could afford to buy two, season, football tickets, one for me and one for a friend, and two tickets to the super bowl. It's no fun going to the game alone.

Or, something that appealed to me more than just possessions, I could have sex. As if I was an Arabian prince, I could have lots of sex. I could have as much sex as I ever wanted with practically anyone and at any time that I wanted. I made a mental list of all the movie stars and celebrities that I'd love to bed.

Only, with me a homebody, instead of having sex with prostitutes, whores, and strangers that I don't know and had no sexual attraction to, keeping my sexual activities close to home, I could have incestuous sex with my relatives. Something more deliciously forbidden, I could have sex with my 46-year-old, MILF of a mother, Mary, my sexy, 21-year-old sister, Rita, my MILF of a 43-year-old aunt, Connie, my slutty, 23-year-old cousin, Jennifer, and my GILF of a 67-year-old grandmother, Ruth.

Something they'd never willingly and consensually agree to having sex with me before, they now may agree to have sex with me for money, for a lot of money. I was willingly going to share my money with them anyway so why not receive something that I wanted in return? Sex. Sex for money and money for sex. How could anyone say no to that? The perfect deal, I needed to have sex with my relatives and, even though they didn't necessarily want to have sex with me, they needed the money. It was a win-win, sexual scenario for both of us.

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My 46-year-old, MILF of a mother, Mary, was the first woman that I took in my confidence and told that I won the lottery. I opened my mother's front door and walked inside her house. Never hearing me come in, she was standing at the kitchen sink washing her breakfast dishes. Dressed in her usual attire after she showered when she had no plans to go out, she wore her housecoat over her bra and panties.

"Mark. What you doing here," she asked turning her head towards me? "Don't you have work today?"

I laughed.

"Work? No more work, Mother. I'm done with working for a living. As of today, I'm officially retired," I said with a laugh.

Clearly, not believing that I was suddenly retired, she made a face as if I was joking.

"Retired? You can't retire? You're only twenty-four-years-old. You have forty more years to work before you can retire and collect Social Security," she said with a laugh. "Besides, what will you do for money? We all need money to live," she said with a sad, little laugh.

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Filled with the sexual, inappropriate thoughts of what I was about to do to and with my mother, I already had a throbbing and pulsating erection from the imagined anticipation of having sex with her. As if I was her husband, her boyfriend, her significant other, or her lover instead of her son, I walked up behind her and pressed myself against her. With her nearly as tall as me, my erect cock fit perfectly in her ass crack through her housecoat and through my jeans. I kissed her neck while wiggling my erect cock deeper.

Curious to see what her reaction would be to me groping her, I reached my arms around her and hugged her while resting my head on her shoulder. I stayed like that for a minute or two while pressing and wiggling myself against her. Then, with her thinking that I was just going to press myself against her while kissing her neck and hugging her, I stealthily moved my hands up to cup her double, D cup breasts. Something that I always wanted to do to my mother, and imagined doing whenever masturbating myself, I was finally doing now.

'I can't believe I'm feeling my mother's big tits through her housecoat and bra. I can't believe she's allowing me to grope her. If I knew that this would be this easy and would be her passive reaction to me touching her and feeling her, I would have sexually assaulted her years ago,' I thought.

As nervous as I was sexually excited, I continued cupping her big breasts in the palms of my hands through her housecoat. I squeezed her tits through her housecoat and bra. With me always staring at the shape and the enormous size of her big boobs, I couldn't believe that I was finally feeling my mother's housecoat and bra clad breasts. Surprising her by my bold, sexual move, she looked down at my hands and then turned her head to look up at me with a smile.

"Mark. What are you doing," she asked with a nervous laugh? "Are you horny," she asked with a dirty laugh? She looked down at my wandering hands again. "Are you having a good time feeling my tits and groping me? You always did like Mommy's big tits," she said turning to look at me again. "You're always staring at them," she said with another dirty laugh.

I returned her laugh with my laugh.

"You're right. I've always loved your big tits, Mom," I said while sliding slow hands across her already erected nipples through her housecoat and bra. I thought about what I wanted to confess before confessing it. "Giving me something to masturbate over, I remember you deliberately me flashing me your naked breasts a few times by not closing your bedroom door when dressing or undressing," I said kissing her neck again while gently humping her housecoat clad ass.

She turned to look at me to make a face.

"I can assure you that I'd never deliberately flash you my naked breasts. If ever you saw my naked tits, obviously, I didn't know you were home," she said as her defense for deliberately flashing me. "If you saw my naked breasts, obviously, you were spying on me."

Yet, she knew I was home. She knew I was standing in the darkened hall in front of her bedroom while watching her undress. Besides, that wasn't the first time that I saw my mother's naked tits. She was always out back sunbathing topless. As if pretending that she didn't know that I was home or pretending that she didn't know that I could see her topless, I'd watch her from my bedroom window rubbing sunscreen all over her big, naked breasts while I masturbated myself.

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A game that she obviously needed to play, I knew my mother was lying about her not knowing that I was home. I knew she was lying about her deliberately flashing me her naked breasts. Perhaps, she deliberately flashed me her tits was because she was horny that day. Perhaps, she deliberately flashed me because she thought that I was horny that day and wanted to sexually tease me. Fully aware that I'd love to see my mother topless, perhaps, she wanted to reward me for something good that I did by showing me her naked breasts.

While still holding her big tits in my hands as if I owned them, I pulled, pinched, and twisted her erecting nipples through her housecoat and bra. She turned off the water and quickly grabbed a dish towel. She dried her hands, turned to face me, and swatted my hands away from her giant breast while laughing. Obviously, even though she acted like she didn't, I could tell that she liked my sexual attention.

"Oh, my God. Mark! Don't do that," she said with a shiver while giving me a flash of sexual arousal.

Then, when I didn't stop but continued, she stared up at me with anger.

"Mark! Stop! What are you doing? How dare you touch me and feel me in that sexual way? What's wrong with you? You shouldn't touch me in that sexual way. That's not right. That's nasty. I'm your mother and not one of your whores," she said. "You make me feel so cheap when you touch and feel me like that."

Not taking her seriously, this was a game that she must play because she's my mother. She needed to protect her morals and modesty. She didn't want me to think that she was an incestuous whore. Yet, instead of apologizing for offending her, I laughed.

"Why not?"

She looked at me as if I had suddenly lost my mind.

"Why not? Because I'm your mother," she said with indignation while folding her arms across her chest to deny me from touching and feeling her where a son shouldn't touch and feel his mother. "Instead of sexually abusing and feeling up your mother, you need to find a woman, Mark. You need to find someone to marry," she said with a nervous, little laugh. "You need to give me a couple of grandchildren to babysit," she said with a laugh.

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Then, with her clearly enjoying my sexy game, daring myself to do so, I reached down and lifted the front of her housecoat to her waist and held it there. I exposed my mother's white, bikini panties to my horny eyes. Then, when she didn't stop me from exposing herself, I reached my hands around her and felt her shapely ass through her panties before I reached in front of her to cup her panty clad pussy in my hand. As soon as I cupped her pussy through her panties, she swatted my hand away while squirming away from me.

"Mark. Stop. Don't do that. What's gotten into? Have you been drinking? Are you drunk? You're making me uncomfortable," she said pushing down her housecoat and closing it. "So, why are you here? You never come here on a weekday at this early hour."

I took her hands in my hands. I lifted her hands to my mouth and kissed them.

"I wanted you to be the first to know," I said pausing while beaming her a wide smile. "I won the lottery. I won the big $320-million-dollar jackpot. After the one-time payout I'll receive $213-million-dollars and after taxes, I'll receive 138-million-dollars," I said.

She put her arms around my neck, hugged me, and then kissed me on the lips. My MILF of a mother kissed me on the lips. Another one of my sexual fantasies come true, I couldn't believe she kissed me on the lips.

Something she had never done before; I couldn't believe my MILF of a mother kissed me on the lips. Daring myself to do so, I was so tempted to part my mother's lips with my tongue. I was so tempted to French kiss her while reaching around her to feel her shapely ass through her housecoat and panties again.

I wondered what it would be like to French kiss my mother. I wondered what she'd do if I tried to French kiss her. I wondered if she'd allow me to part her lips with my tongue, stick my tongue in her mouth, and French kiss her. I wondered if she'd return my French kiss with her long, wet kiss.

"Good for you. That's wonderful," she said.

I took her by her hand and walked her to the living room. We sat on the couch together. Her housecoat was partially unbuttoned where I had raised it. As if she was deliberately flashing me, her knees were parted and her housecoat was raised high enough for me to see her panty clad crotch. When I stared down at her panty clad pussy, she buttoned her housecoat and closed her knees.

"I want to give you some money," I said making eye contact with her. "You'll never have to worry about money again."

She beamed me a smile.

"How much money are you going to give me," she asked?

I smiled at her.

"I want to give you one-million-dollars," I said. "I want to give you one-million-dollars a year for the next five-years, five-million-dollars in total.

She looked as if she was going to faint.

"Five-million-dollars? Wow," she said. "I can finally quit my part-time job at the supermarket."

Mark nodded his head.

"I have only one condition," I said.

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She made a face and wrinkled her brow.

"Condition? I knew there'd be a catch," she said making a face as if I had just burst her balloon. "What's your condition?"

I put my hand on her big breast again. When she didn't swat my hand away, I fingered the impression that her erect nipple made through her housecoat and bra again. Again, she didn't stop me. This time, while staring down at my hand, she allowed me to pull, turn, and twist the impressions of her erect nipples through her housecoat and bra. She was breathing through her mouth instead of through her nose. I had sexually aroused my mother by touching her and feeling her big tits and fingering her nipples.

"I've always been sexually attracted to you," I said. My one condition is this," I said with a long pause while building up the courage to sexually seduce my mother. "I want to have sex with you. I want you to have sex with me," I said looking up at her. "I want you to give me sex, mother," I said pausing while waiting for her reaction to digest what I had just said before continuing. "No one needs to know. It will be our little secret."

She looked at me stunned with her mouth open.

"Sex? You want to have sex with me? You want me to give you sex," she asked in shocked disbelief. "You want to have sex with your mother?"

She looked at me shocked that I wanted to have sex with her. She looked at me as if I was crazy. Yet, she was unable to hide a glimmer of sexual arousal. It was then that I knew that she wanted to have incestuous sex with me as much as I wanted to have forbidden sex with her.

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"What do you mean, when you say that you want to have sex with me? Do you want me to give you a hand job? Is that it? Do you want me to stroke your cock? Do you want me to masturbate you? Do you want me to make you cum? Is that it?"

With her rapidly firing questions at me, clearly, she was nervous. Clearly, I had sexually gotten to my mother. Even through her housecoat and bra, I could see that her nipples were fully erect. I wondered if she was as wet as I was hard.

"Because I can do that? I can masturbate you," she said nodding her head as if she needed that head movement to convince me and/or herself that she'd consensually masturbate me. "To be honest, I wouldn't mind stroking your cock for five-million-dollars," she said with a dirty laugh. "It's been a long time since I've held a hard prick in my hand."

I laughed, too.

"No, I'd want much more than a hand job mother," I said unbuttoning the bottom two buttons of her housecoat and parting her housecoat to expose her panty clad crotch again. "I'd want to undress you. I'd want to slowly strip you naked," I said while cupping her pussy again in the palm of my horny hand through her panties.

Taking a chance that she wouldn't slap my hand away; I slid a slow finger along her pussy slit through her panties. Once again, instead of stopping me, she stared down at my hand. When she didn't stop me from unbuttoning her housecoat and inappropriately sexually touching her pussy through her panties, I unbuttoned the rest of her housecoat. I exposed her bra clad breasts to my horny eyes.