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The big treat came after Sherry passed her commercial pilot’s
check ride. Doris and Janet treated her to a trip to Chicago for
three days of R&R. They took the Bonanza, Sherry flew them to
Meig’s Field right downtown. They went shopping on Michigan Avenue
and in Watertower Place. The highpoint was a theatre night,
including a fantastic dinner afterwards. Sherry was sorry to leave
Chicago, even though she logged some good instrument time,
including a NDB approach to their home base.

Sherry was at the flight school on time. If Craig had any
thoughts about her changed appearance, he kept them to himself.
The classroom phase was over quickly, most of the material was the
same as the instrument course, so they went through it at a fast
clip.
The instructor thought she was a little weak on slow flight
and stalls. “I think you’re afraid of them, so let’s change the
syllabus a bit,” he said. Sherry found herself in the front seat
of a Bellanca Decathalon; they went through stalls, spins, and some
basic aerobatics. She had to use a Sic-Sack on a couple of
occaisions, but soon she was doing loops, rolls, and inverted
flight. Craig had her do inverted stalls and spins, then he let
her take the Decathalon up when she had some free time.
Sherry had the time of her life in the Decathalon. Craig
chewed her ass out for making a low inverted pass down the runway
one afternoon, but she didn’t mind.

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Doris helped Sherry put her clothes away when they returned
to the townhouse. “Tomorrow you start on your commercial pilot’s
license,” she said. “Just be at the flight school by 0730. You’ll
do your training in the Bonanza, since you’ll need to use a complex
airplane for the exam. Wear the jeans and the sneaks for your
flight training. As before, you’ll be flying every other day.
I’ll let you know each afternoon what is planned for the next day
so you can choose the proper attire. If I don’t see you’ I’ll
leave a note in your mail slot.
“The other thing is, you need to start on a physical training
program. Some of that will come later, but I want you to start
running each afternoon. That is to be the only activity where you
aren’t to wear the artificial breasts. Start today.”
“Okay.” Sherry changed into a t-shirt and shorts, then went
out for a run. It was a brief run, she hadn’t been running for a
few months. But she knew from past experience that the wind would
come back quickly.

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Anderson’s jaw dropped. Gazing back at him in the mirror was
an attractive young businesswoman. He ran his hands down the side
of the skirt, feeling the smooth material. He smiled and the woman
in the mirror smiled back. What he didn’t see was the satisfied
grins Doris and the saleslady gave each other. He wasn’t sure how
long he stood there, entranced at his image in the mirror. He felt
something click inside himself, and from then on knew that the
female pronouns were the right ones. It just felt right. It was
a moment that Sherry would remember as long as she lived. She
would later say it felt like she had been reborn.
They spent a lot of time assembling a wardrobe; dresses,
skirts, tops, casual wear, coats, shoes, and a couple of pairs of
boots. Doris picked out a few things to take back with them, the
saleslady promised the rest would be delivered.

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—-
“When there’s nothing else left. You’ll know it, and so will
I. We’ll start on your next visit.”
Doris was waiting in the therapist’s outer office. “What’s
next on the schedule,” Anderson asked.
“We’re going to get you some new clothes.” They rode the
electric jeep to a clothing store. There the saleslady first
fitted Anderson with a bra and a set of breast prothesis. She had
him try on a number of differnt bras, then camesoles and slips.
After that, she brought in a hound’s tooth suit with a white blouse
which she had him try on. Then she fitted him with a pair of black
leather pumps with 3″ heels. Finally, she led him over to a three-
sided mirror.

You’re going to start
spending some time with a therapist to ensure that we aren’t
overloading you. She’ll also help you sort out your feelings about
who you are and what we are training you. Feel free to talk with
her about anything, ok?”
“Sure. Will I still be flying?”
“Oh, yes. You have a *lot* more training to go through.”
The voice coaching was simple. The first session took just
fifteen minutes. The coach showed Anderson how to raise his voice
slightly through humming and gave him a tape-recorder to practice
with.
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The therapist was next. Her name was Janet, she explained
that the process was to talk things out. She would have him
explain his life to her. The process was like peeling an onion,
one removes one layer at a time.
Anderson digested that. “But there’s nothing distinct about
the center of an onion,” he remarked. “How do you know when you
get there?”

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Playful Eye comes to us from the Cascade Bar in Bangkok. We met her one night while drinking…