Chapter 2: (Six months later)
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It has been six months since he woke up that faithful morning and discovered he was no longer the man he once was. Not by a long shot. He no longer was the loser who jerked off every day to his kinky fantasies. In fact, he had no longer jerked off period. He sure wasn’t the loser who won the biggest lottery in history. No, he wasn’t that man at all. He had found that hot escort and made that pact with her to fulfill his kinky fantasy, Then one day she slipped a roofy into his drink and kept him in a twilight dream state after some of the best plastic surgeons money could buy did their magic. When he final woke up he had been transformed into a mesmerizing shemale with D cup tits, sexy puffy lips, a tight waist, curvy hips, creamy skin free of any hair whatsoever and a sexy sultry feminine voice. She told him that his name was now Chastity, Chastity Slavich from Czechoslovakia. How appropriate since his cock had been locked in one of many different styles, materials and colors of chastity cages ever since he woke up that morning.
Speaking of that morning he remembers it like it was yesterday when he saw his Femdom Escort in the mirror behind him with a wicked smile on her face. She reminded him that he did give her permission to be as extreme as possible and he did give her permission to hypnotize him so she could get his inner most secrets and desires. So ever since he has been her shemale sex slave. That day was one he would never forget when she first helped him do his, excuse me, her makeup and lipstick and then she had him/her dress in the lingerie, slutty dress, heels and a blond wig that she had laid out for him/her for the evening festivities. As promised, she had spared no expense for that night’s gala coming out party in his/her honor.
When he/she 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. He was led into the living room by Mistress Vanessa and she introduced him/her 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 amongst them as to who, could 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 off her clothes and put her on her knees. Let the gangbang begin.” He was scared but at the same time excited. All that porn he had jerked off to came in handy because he knew exactly what to do and how to do it. He relaxed and breathed through your nose the first time he deep throated his first cock. He relaxed and didn’t tense when the very first cock slid into his tight virgin ass. The gala coming out gangbang party went on until the wee hours of the morning. He had swallowed loads of cum and cum was leaking out of his ass, but they weren’t done. The party ended with them holding him down while each of them took another turn to shoot their loads all over his 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 Mistress Vanessa didn’t need the money because she had his. She told them Chastity will always be in chastity.
It has been six months since that night, and he/she had sucked and swallowed gallons of cum since. He had even learned to have sissygasms from anal sex that he now looked forward too. Mistress Vanessa was very pleased. In fact, she informed you that he had made her so much money that she hadn’t had to touch his lottery winnings. But first she wanted to make some improvements. She had arranged for the plastic surgeon to give him a cute upturned little nose, some facial cheek bone implants and some hip and butt cheek implants to give him a cuter heart shaped ass. Oh, and she wanted the surgeon to tighten up his asshole. More virgin like was how she described it. She said Chastity would be ready to go in 3 or 4 weeks.
It has been 4 weeks now and even Chastity is impressed at her new look. When she first woke up from surgery the very first thing she did was check to see if Mistress Vanessa hadn’t had his cock and balls cut off. Nope, he was still Chastity locked up in chastity. Since he first woke up that day when he wasn’t servicing her clients, he had told Mistress Vanessa all about his prior life. He told her that he didn’t have any friends per say. He thought the guys at the office would enjoy hearing about his kinky fantasies but most of them considered him a pervert. Except for Jack, who like to hear him go on about dominating a shemale sex slave. Now Mistress Vanessa had a special surprise for him.
She shows him 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 are 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. Get this. In her regular life Mistress Vanessa is a tax attorney. Her secretary, a hot number named Chastity, will be contacting you to set up an appointment to go over 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 identities 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
He reads the letter. Then he reads it again. He is freaking out but then again, he finds himself kind of excited. He, yes, he 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. The bachelor party is in two weeks!”
“By the way, starting tomorrow you will be working in my law office,” Mistress Vanessa says. “Your starting salary will be $60,000 plus benefits. You also will be providing special services on a regular basis too. I will put into trust 40% of those services for your future and 60% to me since I have all the expenses.”
________________________________________
It has been six months since he woke up that faithful morning and discovered he was no longer the man he once was. Not by a long shot. He no longer was the loser who jerked off every day to his kinky fantasies. In fact, he had no longer jerked off period. He sure wasn’t the loser who won the biggest lottery in history. No, he wasn’t that man at all. He had found that hot escort and made that pact with her to fulfill his kinky fantasy, Then one day she slipped a roofy into his drink and kept him in a twilight dream state after some of the best plastic surgeons money could buy did their magic. When he final woke up he had been transformed into a mesmerizing shemale with D cup tits, sexy puffy lips, a tight waist, curvy hips, creamy skin free of any hair whatsoever and a sexy sultry feminine voice. She told him that his name was now Chastity, Chastity Slavich from Czechoslovakia. How appropriate since his cock had been locked in one of many different styles, materials and colors of chastity cages ever since he woke up that morning.
Speaking of that morning he remembers it like it was yesterday when he saw his Femdom Escort in the mirror behind him with a wicked smile on her face. She reminded him that he did give her permission to be as extreme as possible and he did give her permission to hypnotize him so she could get his inner most secrets and desires. So ever since he has been her shemale sex slave. That day was one he would never forget when she first helped him do his, excuse me, her makeup and lipstick and then she had him/her dress in the lingerie, slutty dress, heels and a blond wig that she had laid out for him/her for the evening festivities. As promised, she had spared no expense for that night’s gala coming out party in his/her honor.
When he/she 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. He was led into the living room by Mistress Vanessa and she introduced him/her 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 amongst them as to who, could 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 off her clothes and put her on her knees. Let the gangbang begin.” He was scared but at the same time excited. All that porn he had jerked off to came in handy because he knew exactly what to do and how to do it. He relaxed and breathed through your nose the first time he deep throated his first cock. He relaxed and didn’t tense when the very first cock slid into his tight virgin ass. The gala coming out gangbang party went on until the wee hours of the morning. He had swallowed loads of cum and cum was leaking out of his ass, but they weren’t done. The party ended with them holding him down while each of them took another turn to shoot their loads all over his 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 Mistress Vanessa didn’t need the money because she had his. She told them Chastity will always be in chastity.
It has been six months since that night, and he/she had sucked and swallowed gallons of cum since. He had even learned to have sissygasms from anal sex that he now looked forward too. Mistress Vanessa was very pleased. In fact, she informed you that he had made her so much money that she hadn’t had to touch his lottery winnings. But first she wanted to make some improvements. She had arranged for the plastic surgeon to give him a cute upturned little nose, some facial cheek bone implants and some hip and butt cheek implants to give him a cuter heart shaped ass. Oh, and she wanted the surgeon to tighten up his asshole. More virgin like was how she described it. She said Chastity would be ready to go in 3 or 4 weeks.
It has been 4 weeks now and even Chastity is impressed at her new look. When she first woke up from surgery the very first thing she did was check to see if Mistress Vanessa hadn’t had his cock and balls cut off. Nope, he was still Chastity locked up in chastity. Since he first woke up that day when he wasn’t servicing her clients, he had told Mistress Vanessa all about his prior life. He told her that he didn’t have any friends per say. He thought the guys at the office would enjoy hearing about his kinky fantasies but most of them considered him a pervert. Except for Jack, who like to hear him go on about dominating a shemale sex slave. Now Mistress Vanessa had a special surprise for him.
She shows him 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 are 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. Get this. In her regular life Mistress Vanessa is a tax attorney. Her secretary, a hot number named Chastity, will be contacting you to set up an appointment to go over 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 identities 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
He reads the letter. Then he reads it again. He is freaking out but then again, he finds himself kind of excited. He, yes, he 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. The bachelor party is in two weeks!”
“By the way, starting tomorrow you will be working in my law office,” Mistress Vanessa says. “Your starting salary will be $60,000 plus benefits. You also will be providing special services on a regular basis too. I will put into trust 40% of those services for your future and 60% to me since I have all the expenses.”
