[Fiction] The Lottery Loser

[Paladintwk]

What would you do if you won the lottery?

You have always been a loser with kinky fantasies that you love to jerk off to while watching porn that are related to your fantasies. You fantasize about Femdom domination and have been curious about dominating a shemale yourself. But you're just a loser and porn and jerking off is as close as you will ever get to your fantasies.

Every week you buy a quick pick lottery ticket and every week you lose and go home and jerk off to your fantasies. Then one week you buy your ticket and out of habit just go home, search for some porn and jerk off until your bedtime. The next morning you remember you didn't stay up for the lottery numbers and go online to check your ticket. You check online again to make sure you have the right date. This can't be right. You’re a loser. Losers don't win the lottery, Damn you did. You won the fucking lottery,

You chose to take the one-time cash payment and even accept your check on television. You want everyone to know that you’re not a loser, you're a winner. You're a very rich winner. A rich winner with fantasies to fulfill and you know just where you plan to start.

You get online and find the hottest escort that specializes in your fantasy kink. When you meet her you explain that you want to fulfill some kinky fantasies. She says before you go any further she needs to know more about you and whether or not you can afford her services, You laugh and say don't you recognize me, I'm the big lottery winner and I can afford anything. You hand her your new unlimited platinum American Express card and then hand her $10,000 in cash to boot. You tell her your first fantasy is that you want to be her sex slave. and she has your permission to be as extreme as possible assuring her he can handle anything and if she does you promise to pay more for it again. So the escort agrees and dominates you like crazy for the first couple weeks just to get you well trained for what is to come. When she has you trained and submissive to her will she slips you a roofy and you pass out.

When you finally wake up you are in a dark room in bed. When you get up you noticed that she has you dressed in a sexy bra and panties set, You think to yourself, kinky, this is getting exciting. You find your way into the bathroom to go pee. When you go to pee, you discover she has locked your cock and balls into a chastity cage. You think this really is kinky but at the same time exciting. The chastity cage allows you to pee though. When you get done you turn on the light and look in the mirror and do a double take. First thing you notice is the bra. She must have bought a realistic breast prosthetic to fill out the bra. Then you notice that your entire body is hairless. You look in the mirror and your lips are fuller. This can't be. You quickly remove the bra and to your shock there isn't a realistic breast prosthetic. It's has to be a dream. This can't be real. These D cup tits can't be real. These puffy lips can't be mine. This hairless body has to be a dream. It can't be mine.

Then you see your Femdom escort in the mirror behind you with a wicked smile on her face. She says you did give me permission to be as extreme as possible remember. So now you will be her shemale sex slave that will suck her client’s cocks let them fuck your cute hairless ass. She says you've been kept asleep for about a month and she has had fun spending your money. She says word has it that the big winner of the lottery has gone into hiding because nobody has seen him for over a month. She smiles and says, as she looks at my naked shemale body, and nobody not even you will ever see "HIM" again. Then she tells you first she'll need to help you do your makeup and lipstick and then she has laid out your lingerie, slutty dress, heels and a blond wig for the evening festivities. She has spared no expense for tonight's gala coming out party in your honor. In fact she has invited a dozen of her best clients for your virgin gangbang party. She can't wait to see them rip off your clothes and put you on your knees to suck your first cock of many more to come. Oh, and your new name is Chastity, and it will be that for as long as she wants. At least as long as your lottery winnings last.

[Cactus]

Very hot story! Hope there's more to come.

[Paladintwk]

I am moving the continuation of this story to the Mature Stories thread,