Five years later

Five years had passed since John visited Dr. Valentine for the first time, she fucked his ass, dressed him up as a girl and he got **** by a drunken man. After that John visited her once a week for nearly a year before the therapy ended. Since then she didn't meet John once.

Dr. Valentine left her office after a hard day. She had six patient the whole day, most of them men transitioning to some form of femininity (from crossdressers over shemales to full transgender). With the newest patients she had sex, like usual she being the dominant one. But now she wanted to treat herself to something. In her sexy attire Dr. Valentine drove downtown. There she parked the car and went a minute until she reached a wide area. There were a lot of people walking around, but one woman was standing around like waiting for somebody.

She wore black clothes. Tight black leather hotpants, long black overknee-boots with very high heels going almost all the way up her legs only leaving a small space of her black stocking-footed legs visible, a black jacket with artificial fur with a big cleavage to perfectly show her big round breasts, black leather gloves and a black leather purse. The wind blew through her long blond hair. Her face was perfectly made up and she wore expensive earrings and a necklace. All in all she looked like an escort waiting for her client.

A smile appeared on the woman's face as she saw Dr. Valentine walking towards her. "Dr. Valentine." She greeted the therapist with a smile before they exchanged kiss on the cheeks.

"It's nice to see you again, John." Dr. Valentine greeted the woman. "Oh sorry, you now go by Jenna, right?"

"That's right." Jenna said in a feminine, jet deep voice. "Since becoming a professional three and a half year ago I abandoned my former self and life full-time as a woman."

Flashback

After John had got dressed up as a girl by Dr. Valentine and **** by a man, he visited the therapist weekly. At first again looking like a boy, but after a few weeks he dressed up in the girl-clothes again. From there most of the sessions were about training John to act more womanly, learn how to walk in heels, do his make-up and how to please a cock. To Dr. valentine John said he was still attracted to girls with cocks, but more and more he found himself getting fucked by men, who paid well for it. Dr. Valentine knew John worked unofficial as a prostitute and encouraged him to dress and act more slutty. Then after one year, the therapy had just ended, John was ready and had earned enough money to go to a surgeon and get his first pair of breast implants. Half a year later he had started to official work as an escort at an agency full of shemales. As he was now working as a shemale, he abandoned his old name and went by the name 'Jenna'. He soon had regulars, who spent a lot of money on her and her clothes. Again and again she visited surgeons and feminized her looks. Just three month ago Jenna had her last surgery to augment her breasts to a DD-cup and plump up her lips. Now Jenna was one of the most booked escorts in the agency and in the city.

Flachback end

"You have change quite a lot since then." Dr. Valentine looked over the changed body of the former boy.

"Yes, and I'm happy with it." Jenna replied. "You don't know how much they pay just to spent one hour with a busty blond like me."

"Unfortunately I know how much it is." Dr. Valentine smiled a little embarrassed. She too had booked and paid for the meeting with Jenna.

"Oh yeah, right." Jenna smiled back also a little embarrassed.

"So, do we go?" Dr. Valentine asked after a short silence.

"Yes, let's go." Jenna answered and both women walked down the area.

"I hope you are as big as I remember you are." Jenna teased Dr. Valentine as they walked to the hotel they had booked a room in. "Since then nobody had such a huge cock like you."

"I may be five years older, but down there I'm as big as ever." Dr. Valentine replied with a wicked smile. "So be ready for something huge in your ass."

"Then let's see who has the biggest cock." Jenna grabbed Dr. Valentine's hand and pressed it against her genitals. "Just last year they expanded my cock six times. My clients just love to fuck with a shemale with a huge cock."

"In that case let's have a lot of fun, John." Dr. Valentine smiled and gently squeezed the hard cock in Jenna's hotpants.