The Lottery Loser (Six months later)
The Lottery Loser (Six months later)
It has been six months since you woke up that faithful morning and discovered you were no longer the man you once were. The loser who jerked off every day to his kinky fantasies. The loser who won one of the biggest lotteries in history. No, you weren’t that man at all. You found that hot escort and made that pact with her to fulfill your kinky fantasy, Then one day she slipped a roofy into your drink and kept you in twilight after some of the best plastic surgeons money could buy did their magic. When you final woke up you had been transformed into a mesmerizing shemale with D cup tits, sexy puffy lips, a tight waist, curvy hips, and creamy skin free of any hair whatsoever. She told you your name was now Chastity, How appropriate since your cock had been locked in one of many different styles, materials and colors of chastity cages ever since you woke up that morning.
Speaking of that morning you remember it like it was yesterday when you saw your Femdom escort in the mirror behind you with a wicked smile on her face. She reminded you that you did give her permission to be as extreme as possible. So ever since you have been her shemale sex slave. . That day was one you would never forget when she first helped you do your makeup and lipstick and then she had you dress in the lingerie, slutty dress, heels and a blond wig she had laid out for you for the evening festivities. As promised, she had spared no expense for that night’s gala coming out party in your honor.
When you entered the room that night a dozen of her clients were dressed and anxiously waiting for the surprise that, Mistress Vanessa, that was her name by the way, had promised them. Each had paid her $1,000 deposit for the evening with additional tips expected if they were pleased with the evening. yo were lead into the living room by Mistress Vanessa and she introduced you as follows.
Gentlemen this is my new shemale sex slave, Chastity, She is fresh off her transformation process and has never been touched, In fact she is a virgin shemale who has never sucked a cock or had a cock enter her tight virgin ass. Tonight she is yours and available for the gangbang I promised, For an extra $1,000 one of you can be the first to have your cock sucked and another of you can be the first to pop her cherry ass so to speak. They all jumped at the chance to be first and a bidding war started to be the first. The first cock you sucked brought and extra $5,000 and the first to fuck your ass won the bid at a memorable $6,900. Mistress Vanessa was pleased. Then she said, “Gentlemen please feel free to rip of her clothes and put her on her knees. Let the gangbang begin.” You were scared but excited at the same time excited. All that porn you had jerked off to came in handy because you knew exactly what to do and how to do it. You relaxed and breathed through your nose the first time you deepthroated your first cock. You relaxed and didn’t tense when the very first cock slid into your ass. The gala coming out gangbang party went on until the wee hours of the morning. You had swallowed loads of cum and cum was leaking out of your ass but they weren’t done. The party ended with them holding you down while each took another turn to shoot their loads all over your naked body. Then one of them asked Mistress Vanessa, “How much for the key to her chastity cage? Vanessa responded with her wicked smile that the key was not for sale at any price. After all she didn’t need the money because she had yours’s. She told them Chastity will always be Chastity.
It has been six months since that night and you have sucked and swallowed gallons of cum. You have even learned to have sissygasms from anal sex that you now look forward too. Mistress Vanessa is very pleased. In fact, she informed you that you have made her so much money that she hasn’t had to touch your lottery winnings. Now she has a special surprise for you. Since you woke up that day when you weren’t servicing her clients you have told Mistress Vanessa all about your prior life. You told her that you didn’t have any friends per say. You thought the guys at the office would enjoy hearing about your kinky fantasies but most of them considered you a pervert. Except for Jack, who like to hear you go on about dominating a shemale sex slave.
Mistress Vanessa shows you a letter she sent to Jack via a postal service in Amsterdam, Netherland.
Hey Jack:
I hear your getting married next month. Congratulations. I figure the least I can do for you is use some of my millions to throw you a bachelor party to make your fantasies come true. I wish I could be there but I am spending a year traveling to different countries to see where I finally want to live. I want to live someplace where they ae not hung up on sexual fantasies like they are in the states.
I’ve arranged with this hot dominant escort I met before I disappeared to take care of everything. Her name is Mistress Vanessa and she will be contacting you with the details. She is renting an entire sex club for the night and will be providing stripper/escorts for you and your guest. The theme will be along the lines of “Eyes Wide Shut” so everyone will be wearing mask. Just the mask that cover your eyes. It will put you and your guest at ease knowing their identity’s will be safe.
I’ve asked Mistress Vanessa to find a hot shemale sex slave for you to dominate and live out your fantasies. One that can suck your cock. One that you and your friends can gangbang all night long.
Again, I wish I could be there, but this is the least I can do for you. May all your fantasies come true.
Your friend,
The Lottery Winner
You read the letter. Then you read it again. You are freaking out but then again you find yourself kind of excited. You, yes you will be Jack’s fantasy shemale sex slave. Mistress Vanessa says, “Don’t worry between what I’ve done and the mask I doubt Jack will recognize you. But just incase I will be locking a cock head mouth gag on you and will only remove it so you can suck cocks. You can moan, make sucking noises, cum gargling noises and wincing yelps when that first cock is shoved in your ass too fast but no talking, Understand?”
The bachelor party is in two weeks!
The Lottery Loser (Six months later)
It has been six months since you woke up that faithful morning and discovered you were no longer the man you once were. The loser who jerked off every day to his kinky fantasies. The loser who won one of the biggest lotteries in history. No, you weren’t that man at all. You found that hot escort and made that pact with her to fulfill your kinky fantasy, Then one day she slipped a roofy into your drink and kept you in twilight after some of the best plastic surgeons money could buy did their magic. When you final woke up you had been transformed into a mesmerizing shemale with D cup tits, sexy puffy lips, a tight waist, curvy hips, and creamy skin free of any hair whatsoever. She told you your name was now Chastity, How appropriate since your cock had been locked in one of many different styles, materials and colors of chastity cages ever since you woke up that morning.
Speaking of that morning you remember it like it was yesterday when you saw your Femdom escort in the mirror behind you with a wicked smile on her face. She reminded you that you did give her permission to be as extreme as possible. So ever since you have been her shemale sex slave. . That day was one you would never forget when she first helped you do your makeup and lipstick and then she had you dress in the lingerie, slutty dress, heels and a blond wig she had laid out for you for the evening festivities. As promised, she had spared no expense for that night’s gala coming out party in your honor.
When you entered the room that night a dozen of her clients were dressed and anxiously waiting for the surprise that, Mistress Vanessa, that was her name by the way, had promised them. Each had paid her $1,000 deposit for the evening with additional tips expected if they were pleased with the evening. yo were lead into the living room by Mistress Vanessa and she introduced you as follows.
Gentlemen this is my new shemale sex slave, Chastity, She is fresh off her transformation process and has never been touched, In fact she is a virgin shemale who has never sucked a cock or had a cock enter her tight virgin ass. Tonight she is yours and available for the gangbang I promised, For an extra $1,000 one of you can be the first to have your cock sucked and another of you can be the first to pop her cherry ass so to speak. They all jumped at the chance to be first and a bidding war started to be the first. The first cock you sucked brought and extra $5,000 and the first to fuck your ass won the bid at a memorable $6,900. Mistress Vanessa was pleased. Then she said, “Gentlemen please feel free to rip of her clothes and put her on her knees. Let the gangbang begin.” You were scared but excited at the same time excited. All that porn you had jerked off to came in handy because you knew exactly what to do and how to do it. You relaxed and breathed through your nose the first time you deepthroated your first cock. You relaxed and didn’t tense when the very first cock slid into your ass. The gala coming out gangbang party went on until the wee hours of the morning. You had swallowed loads of cum and cum was leaking out of your ass but they weren’t done. The party ended with them holding you down while each took another turn to shoot their loads all over your naked body. Then one of them asked Mistress Vanessa, “How much for the key to her chastity cage? Vanessa responded with her wicked smile that the key was not for sale at any price. After all she didn’t need the money because she had yours’s. She told them Chastity will always be Chastity.
It has been six months since that night and you have sucked and swallowed gallons of cum. You have even learned to have sissygasms from anal sex that you now look forward too. Mistress Vanessa is very pleased. In fact, she informed you that you have made her so much money that she hasn’t had to touch your lottery winnings. Now she has a special surprise for you. Since you woke up that day when you weren’t servicing her clients you have told Mistress Vanessa all about your prior life. You told her that you didn’t have any friends per say. You thought the guys at the office would enjoy hearing about your kinky fantasies but most of them considered you a pervert. Except for Jack, who like to hear you go on about dominating a shemale sex slave.
Mistress Vanessa shows you a letter she sent to Jack via a postal service in Amsterdam, Netherland.
Hey Jack:
I hear your getting married next month. Congratulations. I figure the least I can do for you is use some of my millions to throw you a bachelor party to make your fantasies come true. I wish I could be there but I am spending a year traveling to different countries to see where I finally want to live. I want to live someplace where they ae not hung up on sexual fantasies like they are in the states.
I’ve arranged with this hot dominant escort I met before I disappeared to take care of everything. Her name is Mistress Vanessa and she will be contacting you with the details. She is renting an entire sex club for the night and will be providing stripper/escorts for you and your guest. The theme will be along the lines of “Eyes Wide Shut” so everyone will be wearing mask. Just the mask that cover your eyes. It will put you and your guest at ease knowing their identity’s will be safe.
I’ve asked Mistress Vanessa to find a hot shemale sex slave for you to dominate and live out your fantasies. One that can suck your cock. One that you and your friends can gangbang all night long.
Again, I wish I could be there, but this is the least I can do for you. May all your fantasies come true.
Your friend,
The Lottery Winner
You read the letter. Then you read it again. You are freaking out but then again you find yourself kind of excited. You, yes you will be Jack’s fantasy shemale sex slave. Mistress Vanessa says, “Don’t worry between what I’ve done and the mask I doubt Jack will recognize you. But just incase I will be locking a cock head mouth gag on you and will only remove it so you can suck cocks. You can moan, make sucking noises, cum gargling noises and wincing yelps when that first cock is shoved in your ass too fast but no talking, Understand?”
The bachelor party is in two weeks!
