literature
Crossdresser's Paradise
Literature Text
Crossdresser's Paradise
by RogerGirl
Charles had just returned from his summer trip with Stan and Desiree. It was a rare time of year since both his parents were home at their main mansion. Charles was feeling nervous, but felt he had to finally tell his parents about Charlene, his feminine side, and that he was bisexual. He walked into the kitchen where his parents were eating lunch. His father, Simon, came from a long line of wealthy businessmen and had expanded his family's businesses into the empire that Charles was set to inherit after his parents retired. His mother, Jenna, was a former model who eventually entered one of Simon's companies after going to college. She worked her way up through the company and was now an executive. In public, his parents were known for both their business savvy and their eccentric lifestyles. They owned houses all over the world, several private jets, many cars, resorts, ships, yachts, a hot air balloon, a blimp, a zeppelin, a private island, and a space retreat. Despite their wealth, however, they both had a strong work ethic and made sure Charles got a strong education and actually learned the family's businesses. They had gotten married when Simon was 22 and Jenna was 20 and Charles was born a year later.
"Hello son," his father said looking up from his iPad, "how was your trip?"
"It was fun," Charles said, "but there's kind of something I wanted to talk to you both about."
"What is it?" his mother asked concerned.
"Remember the prom at The Academy?" he asked his father.
"Yes, quite well," his father replied.
"Well, I went to the prom with Stan," he continued, "and I played the girl."
"That's nothing to be embarrassed about," his father said, "I went to one of my proms there as Simone and had a lot of fun."
"Yes, but that wasn't the last time I dressed as Charlene," Charles stammered, "I've been becoming Charlene in private ever since then."
"Do you want to become a girl?" his father asked.
"No, I like being a boy," Charles answered, "I just have fun dressing up as Charlene from time to time. And I think I'm bisexual."
"Why do you think that?" his mother asked.
"I've been dressing as Charlene to be with Stan," he continued, "but I am also in love with Stan's sister, Desiree. I mostly like girls, but I also love how sexy I feel when Stan kisses me when I'm dressed as Charlene."
"Well, that was very brave of you," his father said, "I know how hard it was for you to tell us and we want you to know that we stand by whatever decision you decide to make. I think this would be a good time to let you in on our secret."
"Secret?" Charles asked curiously.
"You see," his father went on, "I didn't only dress as Simone for the prom. I too continued dressing in private at every chance I got. After graduation and after college I decided to create a place where I and others like me could indulge in their feminine or masculine sides in private without judgement from society. While I also have no plans to become a woman, I know how great it feels to be able to walk around in a public place with others who also enjoy becoming the opposite gender from time to time."
"Wow," Charles responded surprised at what his father had just told him, "could we visit there sometime?"
"Of course," his father replied, "the private island is an invitation only safe haven where crossdressers are free to do whatever they want. While most of those who visit are straight, some are gay or bisexual. If you would like, you could vacation there as Charlene. Everyone there is there for the same reason, so there is no need to be afraid of anything that happens there being revealed to the public."
"We're proof of that," his mother said, "your father and I have been vacationing there for years and have enjoyed great times together. You may not realize this, but your father makes a very beautiful woman. Spending time with Simone is part of what has kept our marriage strong for so many years."
Charles thanked his parents and they continued talking. Charles eventually dresses as Charlene for his parents and his father dressed as Simone for him to see. They would begin traveling to the island together from time to time and Charles would sometimes take private vacations there with Stan or Desiree or both. Charles would also find other crossdressers and send them private invitations to the island. Through Desiree, Charles would make friends with a group of crossdressers whom he would invite to the island. In a future story, we'll see Charles, Desiree, Stan, Jamie, Allen, Anna, Steven, Kristen, Madison, Eric, Danny, Reggie, Dennis, Sarah, Nick, Monica, Marcus, Kyle, Kelly, Courtney, Ron, Shannon, Kelsey, and a few others from previous stories get on one of the Kaplan family's private jets for a week in a Crossdresser's Island Paradise.
by RogerGirl
Charles had just returned from his summer trip with Stan and Desiree. It was a rare time of year since both his parents were home at their main mansion. Charles was feeling nervous, but felt he had to finally tell his parents about Charlene, his feminine side, and that he was bisexual. He walked into the kitchen where his parents were eating lunch. His father, Simon, came from a long line of wealthy businessmen and had expanded his family's businesses into the empire that Charles was set to inherit after his parents retired. His mother, Jenna, was a former model who eventually entered one of Simon's companies after going to college. She worked her way up through the company and was now an executive. In public, his parents were known for both their business savvy and their eccentric lifestyles. They owned houses all over the world, several private jets, many cars, resorts, ships, yachts, a hot air balloon, a blimp, a zeppelin, a private island, and a space retreat. Despite their wealth, however, they both had a strong work ethic and made sure Charles got a strong education and actually learned the family's businesses. They had gotten married when Simon was 22 and Jenna was 20 and Charles was born a year later.
"Hello son," his father said looking up from his iPad, "how was your trip?"
"It was fun," Charles said, "but there's kind of something I wanted to talk to you both about."
"What is it?" his mother asked concerned.
"Remember the prom at The Academy?" he asked his father.
"Yes, quite well," his father replied.
"Well, I went to the prom with Stan," he continued, "and I played the girl."
"That's nothing to be embarrassed about," his father said, "I went to one of my proms there as Simone and had a lot of fun."
"Yes, but that wasn't the last time I dressed as Charlene," Charles stammered, "I've been becoming Charlene in private ever since then."
"Do you want to become a girl?" his father asked.
"No, I like being a boy," Charles answered, "I just have fun dressing up as Charlene from time to time. And I think I'm bisexual."
"Why do you think that?" his mother asked.
"I've been dressing as Charlene to be with Stan," he continued, "but I am also in love with Stan's sister, Desiree. I mostly like girls, but I also love how sexy I feel when Stan kisses me when I'm dressed as Charlene."
"Well, that was very brave of you," his father said, "I know how hard it was for you to tell us and we want you to know that we stand by whatever decision you decide to make. I think this would be a good time to let you in on our secret."
"Secret?" Charles asked curiously.
"You see," his father went on, "I didn't only dress as Simone for the prom. I too continued dressing in private at every chance I got. After graduation and after college I decided to create a place where I and others like me could indulge in their feminine or masculine sides in private without judgement from society. While I also have no plans to become a woman, I know how great it feels to be able to walk around in a public place with others who also enjoy becoming the opposite gender from time to time."
"Wow," Charles responded surprised at what his father had just told him, "could we visit there sometime?"
"Of course," his father replied, "the private island is an invitation only safe haven where crossdressers are free to do whatever they want. While most of those who visit are straight, some are gay or bisexual. If you would like, you could vacation there as Charlene. Everyone there is there for the same reason, so there is no need to be afraid of anything that happens there being revealed to the public."
"We're proof of that," his mother said, "your father and I have been vacationing there for years and have enjoyed great times together. You may not realize this, but your father makes a very beautiful woman. Spending time with Simone is part of what has kept our marriage strong for so many years."
Charles thanked his parents and they continued talking. Charles eventually dresses as Charlene for his parents and his father dressed as Simone for him to see. They would begin traveling to the island together from time to time and Charles would sometimes take private vacations there with Stan or Desiree or both. Charles would also find other crossdressers and send them private invitations to the island. Through Desiree, Charles would make friends with a group of crossdressers whom he would invite to the island. In a future story, we'll see Charles, Desiree, Stan, Jamie, Allen, Anna, Steven, Kristen, Madison, Eric, Danny, Reggie, Dennis, Sarah, Nick, Monica, Marcus, Kyle, Kelly, Courtney, Ron, Shannon, Kelsey, and a few others from previous stories get on one of the Kaplan family's private jets for a week in a Crossdresser's Island Paradise.
Crossdresser's Paradise
By rogergirl