The Big Winner
by Jennifer White
Michael was scanning through the paper, when he saw a face from his past. Alicia. The girl he had loved from afar, for as long back as he could remember! He was still single, never having found anyone who come make him feel in his heart what *she* could. And now, she was famous. She was in the paper, because she had just won a lottery jackpot of 25 million! She was still beautiful, still perfect, and now she was rich.
Michael though back about all the times he had wanted to approach her, but had been too shy. He had been scared, and had let opportunity after opportunity slip away. Yes, he wrote her a few letters, but she ignored them. She had never responded to that, but at least she knew how he felt about her!
He read the whole story twice. She was single herself, and living in the next town over, just a short drive away! Michael was suddenly overcome with his feelings. He *had* to have her. He was afraid that by now, she'd be married and have several children. But she was still single. Now that she was rich too, she'd be getting suitors by the dozens. He had to act fast! He had to act *now*.
* * *
Michael took a deep breath as he parked his car across the street from Alicia's house. It took a little work, but he had found her address through an internet search. Now he was there. Nobody was around, not even a reporter. And the light in the upstairs bedroom suddenly came on, telling him that she was indeed home.
It was the hardest thing he ever did, finding the courage to stand up and walk up to her door, then ring the doorbell. But he *had* to. This was his one chance in life to find true love, with the one woman he ever fell for. And it didn't hurt that she was now super rich! His leg was trembling as he stood there, holding a bouquet of flowers, waiting for her to answer the door.
The door swung open, and there she was! A few years older, but looking just as good as ever. Alicia!
"I know you..." she said, staring at Michael. Suddenly, it dawned on her. He was the shy nerdy guy she knew from way back at school! Here at her doorstep, with flowers for her. Just like all of the other guys who were suddenly interested in her, now that she was rich. What were these men thinking? That she'd see them, fall for them, and jump into their arms? They were just hitting on her because she had won the lottery. They didn't care about her! They just cared about the money.
"Alicia" said Michael. "It has been a long time since I've seen you."
"Yes, it has" she replied, curtly.
"I know that you probably don't believe me" he said. "But I do love you. I always have. Do you remember the notes I sent you, back in school?"
"How could I forget" she replied, thinking of his awkward attempts to write love poetry to her, telling her how he loved her so much, even though he didn't even know her! How could he think that she'd respond, when they weren't even friends? How naive of him. And here he was, trying to hit on her again, no better than he was back in school.
"You think I'm like all the others" he said, his head lowering in dejection. "I didn't come here to see you just because you're rich now. I came here because the news item in the paper was the first I heard about you in years. I thought by now you'd be married and have children. I didn't want to bother you, so I never tried to see you. But when I read you were still single...."
"I was about to be married" she said. "But one day, I found out that I had a 'female' problem, and I needed to have my ovaries and my uterus removed. I can never have babies. My fiancee dropped me, and I've never had a serious suitor since."
"I'm so sorry" said Michael.
Alicia half-expected for him to want to leave also. What man didn't want to have children some day? But he stayed there, as if he wanted her to let him inside. She was exasperated with all of the men who were suddenly interested in her. A few days before, nobody cared, but now she was swamped. She hated them all, since they were phonies. And worst of all: she knew that they'd keep coming to her, again and again, seeking a way to get to her money. Already, she had stopped answering her phone, letting her machine screen the calls. She was getting swamped with letters in the mail, and people knocking at her door. All because she was a rich, single woman.
But then, she had a though. If she was a rich *married* woman, these desperate men would leave her alone. Then she could live her life in peace. An idea formed in her head. She looked at Michael, and smiled.
"You once wrote me that you wanted to marry me. Is that still true?" she asked.
"Yes!" he replied, almost unable to believe his ears.
"Come back tomorrow afternoon at 5:30. Don't worry that the house will be surrounded by reporters. Just come knock on the door. I'll see you then. And bring flowers!"
"Okay..." he said, as she closed the door on him.
Michael was walking on air as he returned to his car. He was going to have a date with Alicia!
* * *
Michael hardly slept all night, he was so excited. He took the day off of work, so he could be sure he was ready for his big date. As Alicia had suggested, he went to the store and bought a dozen red roses for her. He put on his best suit and tie, then drove to her house. Just as she had predicted, there were dozens of reporters outside, and he had to park down the street!
He proudly walked up to the door, as flashes from the cameras burst in his eyes, making him see stars. He rang the doorbell, and moments later, Alicia opened it up. She was wearing a white full length dress, and she looked stunning. He handed her the roses, and she smiled, giving him a kiss as the cameras clicked away at full speed.
"Gentlemen, this is my old highschool sweetheart, Michael" she said to the reporters. "We're going to get married!!!!"
There was some applause, as more pictures were snapped. The reporters and cameramen then scattered, each wanting to be the first to write up a report about how the new millionaire was about to marry her old highschool sweetheart. It would be in every paper, by the morning. Alicia knew this. Her plan was coming together perfectly. But tomorrow, the flood of suitors would grind to a halt.
"Did you really mean that?" he asked her, once they were inside, with the door locked. "Are we really going to be married?"
"Yes" she said. "As long as you're willing to do what it takes to become mine."
"I'm willing. Whatever it is!" said Michael.
"As you know, I've been on my own for quiet some time" said Alicia. "I am used to running my house the way that *I* want it run. And now that I have all this money, I'm going to want to have complete control over it too. Are you willing to marry me, knowing that *I* will be the one who controls everything, and makes all of the decisions?"
"Yes" said Michael, without even thinking. He'd do anything to be with her!
"Really?" she said. "I need to put that to the test. I need you to come up to my bedroom, so we can see if you are really able to live up to your word."
"I swear it" he said.
"Michael, are you willing to completely surrender to me?" she asked. "Are you willing to become all mine?"
"Yes Alicia, I am" he said.
"Then take my hand, and lets take the first step towards you becoming mine" she said.
He took her hand, and she led him up to her bedroom. It was beautiful, with antique furniture, including a canopy bed covered in a white lacy cover that matched the lace curtains. The walls had a faded pink tint to them. Everything had such a feminine look to it! But Michael barely noticed: he could hardly take his eyes off of Alicia.
She turned to him now, and reached around behind herself to undo her dress. It dropped down to the floor, revealing what she had on underneath: a black vinyl cat suit, with high heel boots. She took her hair, and pulled it back into a tight ponytail, then she turned to face him.
"Take off all your clothes" she said. "Now!"
Michael almost jumped, he was so startled. He had never seen her dressed like that. She looked so hot! When she ordered him to strip, he was so surprised! As quickly as possible, he removed everything, until he was down to just his boxers.
"And those too" she said. "I told you to take *all* of your clothes off. Don't ever disobey me again."
"I'm sorry..." he stammered, as he removed his boxers. Now he was there, naked in front of her. She took confident strides, walking around him, inspecting him from all angles. She walked over to her dresser, and opened up a drawer. Michael watched as she removed something that looked like a large black dildo. He was horrified to watch as she held it in front of her, right over her pussy, and turned it until it clicked and locked in place. Now it looked as if she had a large erect penis poking out in front of her!
She pointed to the floor in front of her.
"Kneel" she said, firmly. With his knees feeling weak already, Michael almost collapsed to the ground. Now he was looking *up* at her, seeing her large fake penis pointing right towards his face. As he stared at her, gaping, she took out a tube and squeezed some white cream onto the tip of her strap-on. Then she took her hand, and started move it up and down, as if she was a man jerking off. Her eyes closed as if she was feeling deep pleasure, as she spread the white cream all over her fake penis.
Alicia now took something from the drawer, and held it out towards him. It looked like a black leather dog collar, but very large. It had metal studs on the sides, and it was about two inches wide. She held it out for him, and slipped it over his head. She was so close to him that he could feel her body heat, as she started to tighten it.
"You are becoming mine now. Go to the bed" she said. "Lift back the cover, and put your hands on the bed."
Michael stood up, and went over to the bed. He did as she asked, removing the cover. There on the bed, he saw all sorts of feminine things. Bras. panties. Nylons. Tampons. Garter belts. And more. He put his hands on the bed as she asked, wondering what in the world she was doing.
"Now move your legs further apart, and lean over. Further! Spread them more!"
Michael did as she asked, feeling very uncomfortable and vulnerable. His worst fear came true, as he felt the tip of her strapped-on fake penis start to explore him in his rear. Alicia pushed it into him about half an inch, and he felt an involuntary jerk of his muscles, trying to stop her from penetrating him.
"Don't resist me" she said. "Let me in, all the way. Show me that you are mine now."
Michael was all tight, and he couldn't relax. How could he?
"Surrender to me!" said Alicia. "Once I'm inside you, you will be completely mine. You said you loved me. You said you'd do whatever I needed. *This* is what I need Michael. She me you are mine. Give yourself to me, completely."
She pushed forward harder, and he could feel her penis slide further into him. It was somewhat painful as she pulled back a bit, then thrust forward hard, driving it deeper into him..
"You are becoming all mine" she said. "I'm going inside of you. That's right. My dick is deep inside of you now. Soon, you're going to *like* this, and beg for me to do this to you all the time. Soon, you'll *want* to suck my dick, as I turn you into my slave. You want to show me how much you're mine. Surrender to me completely, and show me you want to be mine."
Michael almost shed a tear as he relaxed for a moment, just enough, for her to get the full length of her enormous strap-on into him. Now fully inside, she started to rock back and forth, thrusting again and again, pounding him into submission. After ten minutes, she stopped, but she was still inside of him.
"Take the bra off the bed" she said. "Pick it up, and put it on yourself."
Michael felt so foolish, but he did as she had commanded. It was hard, leaning over the bed, with her dildo inside him.
"This is to show you that you *will* do anything I order" she said. "And also to make sure that you understand your place. Tell me, my dear, in a marriage, who is it that puts their dick into their partner?"
"The husband?" he said, his voice trembling.
"Exactly. And who is it that is on the receiving end?"
"There. Now you understand. In our marriage, I am going to be the husband. And *you* will be the wife."
Michael couldn't believe what he was hearing! How could his sweet Alicia be saying this? As he contemplated what was going on, she reached around him, and pulled the left cup of his bra away from his body. Into the gap, she pressed something in, to fill up the cups of his bra. It looked just like a woman's breast, and it was at least D-cup sized. Michael gasped as she did the same on right side.
Not only was he wearing a bra now, but it was full to the bursting point with large, realistic looking breast forms. Alicia cupped her hands around them, and began to thrust into him again, harder and harder. He was going to be Alicia's wife? She wanted to be his *husband*? Fear gripped him, and he didn't even know what to think, let alone how to act.
"Mmmm" she said. "I love to see you looking so feminine, with big boobs filling out your bra, and a dick up inside of you. Lets see what else we can do now."
Thankfully (for Michael), she withdrew the strap-on from him, and he was finally able to stand up. Part of him wanted to run away from her, but how could he do that wearing nothing but a bra, filled with the huge fake breasts? He could only stand there as she held out a pink cami, and started to put it on him. It had white lacy trim, and it was all shiny and soft. Michael's eyes were bugging out of his head when he saw it on himself, his new large fake breasts forming large pink mounds on his chest.
"A pretty girl like you should have pretty hair" said Alicia, as she gripped her strap-on, as if she was making herself get hard again.
Michael's knees went weak. She had just called him a girl! She pointed to the bed, and he resumed his former position. Once again, she entered him. But this time, there was no resistance. She slid it in easily, going in deeply on the very first try.
"See?" she said, "You have completely surrendered to me already. You have already given yourself up to me. You have already accepted the fact that from now on, you are going to be a woman."
Michael felt her hand reach around him, and squeeze his penis. He couldn't help but to get hard from all the stimulation. As she continued to thrust into him, she kept telling him that he was a woman now. And against his will, he suddenly came, making quite a mess on the bed. He was almost in tears now, and offered no signs of resistance as she handed him a pair of panties to put on, followed by a white skirt.
"You are my slave now" said Alicia. "And to remind you that you're mine, and that you're being turned into a woman, I have decided that from now on your name will be Sara."
"Sara?" he asked, shocked.
"You are Sara now. You are my woman. And you are my slave."
Michael did start crying now.
"Just like a woman" scolded Alicia. "So emotional. Oh, by the way, I forgot to tell you. See that thing in the corner there? This whole episode was captured on camera. If you even think of running away or disobeying me in any way, I will make sure that everyone sees your film, with you losing your virginity to my dick. I control you completely now. You *are* mine. Now get down on the floor, and lick my boots to show me that you understand your new place in the world, as my slave."
Michael's knees buckled. He fell to the floor, and did as she asked.
"Good" she said. "Good girl. Of course, if you're not good, I will make you sleep in a cage at night. Or you can be a good girl, and obey me. Do you promise that you'll be a good girl for me, Sara?"
"You need to tell me" she said.
"I'll be good" he said, his voice a hoarse whisper.
"A good what? Say it louder!"
"I'll be a good girl" he said.
"Wonderful! Then you can start by going to take a shower, and removing all of that nasty hair on your body. Now that you're a woman, you can't go around with hair under your arms and on your chest! Don't for get those legs of yours either. When you're done, there is some nice body cream on the counter, to make your skin nice and soft. Then you can dress up in the pretty things I've got laid out for you."
Michael did as Alicia had ordered, and he was horrified to see the lingerie set he was to put on. It was ultra-feminine and ultra-sexy, all white with lace, silk and frills. He was puzzled that she left a note *not* to put in the breast forms. Instead, he was to put on a suit which he recognized to be a *women's* suit, but one that was quite androgynous. The shoes with it weren't quite manly, but weren't overtly feminine either. He put it all on, and went out to present himself.
"We're going to see the judge now" she said. "He will marry us. In less than an hour, we will be husband and wife, legally."
It was his dream come true, but also a nightmare! Hand and hand they walked into the courtroom, and signed the papers. The judge was all business, swiftly conducting the ceremony so that he could get on with his busy day. With a signature from him and an official stamp, it was done. Michael had just married the girl of his dreams, Alicia.
They returned home, and she led him up to her bedroom. She smiled as she started to remove her own clothes, and then his! She went down on him, getting him as hard as a rock. Then she leaned over the bed, and spread her legs wide open.
"Put it in me, baby" she said. "I like it from behind."
Michael wasn't sure which hole she wanted him to use, but her hand guided him into her wet pussy. What heaven it was to be inside her after all those years, even if he was still dressed all in fine white lingerie, and even if she was calling him "Sara" as he started to rock himself in and out of her.
Finally, Michael's years of desire for Alicia poured out all at once, as he throbbed inside of her. She purred, as she waited for the last drop to come out.
"That was the one and only time we will ever make love, with you inside of me" she said. "From now on, it will be me inside of you, as I'm about to do to you now."
She put her strap-on back on, and made him lay on the bed, right on the edge. She positioned him so that she could be on top, and enter him. She handed him his huge breast forms, and ordered him to put them in. As soon as they were in place, nestled inside his bra, she began applying the cream to her big fake dick, and then she put it into him, as she had done before in the day.
"You are my wife now" she said. "And *I* am the husband. *Your* husband. You belong to me now. Legally, we are married, so that no man will ever bother me again. But don't ever think, even for a moment, that you have any power over me. All of the power is mine. You are mine. My slave. You are Sara now."
Michael could only lay there, and let her continue to thrust into him.
"I'm putting you on female hormones, so your body will begin its feminization process. I'm going to make you grow *real* boobs, so you won't need your forms anymore. I'm going to give your curves. I'll pluck your eyebrows, pierce your ears, and make you look so feminine and so sweet. You are Sara now, and you are my slave."
"You will get up every morning at 4:30am. You will dress up as my maid, and you will do my housework, make the breakfast, rub my feet, and do anything I tell you. You live for me now, and you will obey me in all things. Tomorrow, we'll go to the store so you can buy yourself dildos, vibrators, and gay porn magazines, so you can amuse yourself as I turn you into a woman. From now on, you'll be having a lot of dicks in your mouth, and up inside you, as I am now."
She thrust forward harder and harder.
"You're a woman now! You are Sara! You are my wife! And you are my slave."
Michael couldn't help but to feel pleasure, as she pushed in deeper and deeper. He was wish his beloved Alicia now. Now and forever. He loved her with all his heart! He would do anything for her, even this. If being her wife was what *she* wanted, then it was what he wanted too.
"I love you" he said. "I'll try my best to make you happy, and to be a good wife for you."
"I know you will" she said. "I know you will."
Alicia had it all now. Riches beyond her dreams, a live-in maid, and a devoted wife who loved her, with all his heart.
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