First Time in the City

A garter belt and black nylon stockings were laid out on the bed for Michael, as well as a black slip. Sharon helped Michael put the garter belt on and carefully rolled Michael's stockings up and attached them to the clips on the belt.

Finally, it was time for the dress. Renee had picked out a red silk dress. She helped Michael put it on so he would not mess his make-up. The hem of the dress fell just below Michael's knees.

Renee helped Michael put on a pair of three-inch black heels with an ankle strap. Luckily, Michael was not tall, only 5 foot 8, so the heels did not make him overly tall. Renee instructed Michael on walking in the heels, showing him how to walk like a woman rather than with the clumsy gait of a man. Michael was not quite perfect at it, but it would have to do.

It was 4:45 and the work on Michael was done. He looked at himself in the mirror. He loved what he saw. A beautiful woman in an amazing red dress. Michael started to tear up, but Renee quickly brought him a tissue so he would not ruin his make-up.

It was time. Renee gave Michael final instructions, "Tonight your name will be Julia. Mr. Dollinger likes that name and thinks it fits you. You should not have to say much, but if you do, keep your words to a minimum. You look beautiful, Julia." Renee kissed Michael on the cheek.

With that, Renee left the room. Felice and Sharon had already packed up and left. Michael was alone. He sat down in a comfortable chair, crossed his legs, straightened his dress and waited for Mr. Dollinger.

Mr. Dollinger arrived promptly at 5:00 p.m. He was dressed impeccably in a navy suit. He walked into the room and kissed Michael lightly on the lips. He said, "Hello, Julia, you look stunning." Mr. Dollinger handed Michael a box. He opened it and it had an exquisite diamond necklace in it that perfectly matched his earrings.

"Do you like it, Julia?" Mr. Dollinger asked.

"I love it, sir," Michael responded. He tried to keep his voice quiet, practicing.

"Good, then let's go have some fun, Julia," Mr. Dollinger said. He laced his fingers into Michael's hand and walked him out of the room to the elevator.

Drinks and dinner went off without a hitch. Mr. Dollinger was meeting with several Chinese businessmen to discuss a deal. They all had dates with girls in their twenties. If they noticed anything special about Julia, they said nothing. Michael had an amazing time.

Around midnight, Mr. Dollinger and Michael walked back to his suite. Mr. Dollinger held Michael's hand the entire way. He had been a complete gentleman all night.

When they got back to the room, Mr. Dollinger said, "You were lovely tonight, Julia. Absolutely lovely."

"Thank you, sir," Michael replied.

Mr. Dollinger continued, "Julia, I would like nothing better than to bend you over that bed and fuck you. You are an incredibly sexy girl. But, I don't think you are ready for that."

Michael's cock strained against the gaffe. He wanted Mr. Dollinger to fuck him. He wanted it more than anything right now.

"I talked to your boss at length today, Julia. He is aware that Michael has decided to transition. He is perfectly happy with that and he is looking forward to meeting Julia and getting to work on the new accounts," Mr. Dollinger said.

Mr. Dollinger continued, "I have taken the liberty of shipping a new wardrobe to your home. I have arranged a first class ticket for you to fly home tomorrow. In a couple of days, I will send Sharon and Felice down to help you for the next month with your make-up and hair. I know you have a lot to learn."

"Thank you so much, sir," Michael said. He was nearly in tears.

"You're very welcome, Julia. I am sure you will be quite happy now," Mr. Dollinger said, "And Julia, I have sent some things to your home so you can prepare to be fucked. You should practice with them. I am very much looking forward to fucking you the next time I see you."

Michael wanted to be fucked by Mr. Dollinger very badly.

Mr. Dollinger unbuckled his belt, and dropped his pants and underwear. His cock was beautiful and hard. "Come here, Julia," he said.

Julia did not need to be asked twice.