Steve Hardman was a billionaire at just age 35. He made his fortune in the cryptocurrency craze of the early 21st century. He's also 6 foot 3 inches of lean muscle, always keeping himself in great shape. He generally splits his time between NYC where his 60th floor penthouse has a commanding view of Central Park, and the rest of the year is spent at his mansion in Marin County, California. He's a lifelong bachelor and has had no long term girlfriend. And to be honest, he prefers it that way. He prefers the playboy lifestyle and he can easily afford it.

Maria Alexander is a high class escort. She had her son Timmy when she was just 18 years old, and kept escorting after she gave birth. The father was one of her clients, who quickly skipped town and she never heard from again. Despite being a single mom, she was happy with just herself and her son. Marina eventually got into porn, which allowed her a more luxurious lifestyle. She had a nice condo in Los Angeles with a sweeping view of the city, and she drove a fancy BMW that was given to her by a client. Life was good for both of them.

She knew of her son's sissy and girly ways from an early age, and encouraged him to be as femmy as possible. She bought him girls clothes, taught him how to do makeup, and they played dressup and fashion games from an early age. At age 11, he really got into being a girl as much as he could, and Maria helped him set up a web site. Coming up on his 12th birthday, he told her that he wanted to be a fashion model and be a girl full time. Although shocked at first, Maria quickly embraced the idea, and came up with a plan to help. They were able to acquire puberty blockers and hormones over the internet, and she started the feminization process on his 12th birthday. With the financial support of Mr. Hardman, she was able to start having him home schooled instead of going to public school for the 7th grade.

Timmy had been as fem as he possibly could get away with, even at school. His hair was long and he regularly kept his brows plucked. He would do things like wear girls sneakers and jeans to school. Most of the kids thought he was weird, but they didn't tease him about it. Whe he started a modelling page on the internet as his alter ego Tiffany, no one at school caught on that it was actually him.

Her web site was a modelling portfolio, where customers could pay a monthly fee and download modelling sets and short videos. Her customer base was varied, but was mostly men who are tuned on by young femboys or transgirls. She would have weekly chats with the highest paying customers, and would model clothes that they sent to her mother. She would model everything from innocent schoolgirl outfits, to girly anime characters, or more revealing sets for her more elite customers. After around 6 months on her illicit hormone regimen, Tiffany had 2 small but definite breasts, and her hips started to fill out. She was starting to look less like a 12 year old boy and more like a 12 year old girl, with the curves and soft skin that would be expected of a girl that age.

One of her most daring photosets came out at this time. In it, she was expertly made up with deep red lipstick, dark eye makeup, expertly shaped eyebrows. Her light blonde hair was in a bob, and she wore a black choker and silver hoops in her ears. Her bra was black satin with tiny cups that barely covered you young growing breasts. She had on a black satin garter belt attached to sheer real silk stockings, and her feet were shiny black high heel pumps, the kind you would typically see on a high class porn star. Her black satin panties left no room to the imagination and you could clearly see that she had a small feminine penis. Although with the hormones she was on, she would never get a bigger cock, she could still get hard and she was definitely excited in this shoot. Most of her fans really loved this, by the way. The set featured her posing in suggestive poses that showed off her young developing body, which by this age she was keeping completely hairless except for the hair on her head. It secretly made her hot thinking about all those men that are turned on by her photosets. During their members only chats they would sometimes ask to do more illicit things. The chats were supposed to be monitored by mom, but when certain elite customers came on, she would just tell Tiffany to be a good girl and that she trusts her judgement. Tiffany was elated by this because she knew she could make more tips with these guys, and also because more and more she was starting to get turned on by the thought of getting fucked by one of these successful rich businessmen. She was especially attracted to Mr. Hardman.

With her mom's help, she was starting to bring in enough money that her mom vastly cut back on her escorting activities, but she did still see some elite clients. One of those clients just happened to be Mr. Hardman. Maria had known that Mr Hardman had a thing for young tgirls, and she told him about Tiffany, the site, and everything. She explained to Mr. Hardman that she couldn't date the first year she was on hormones, but that when she is 13 that she can make her own decisions. Mr. Hardman secretly thought that she was the mom of the year.

To be continued...