Ladyboy 69 Blog

Col Hampton mulled that over. “How’s the flying coming?”
Doris fielded that. “Craig says she’s doing well. She may
not be a pure natural at it, but she is working very hard at it.”
“So, what’s the next step in her training?”
“She’s started multi-engine work. Once she gets her multi
ticket, then we are going to get her rated in DC-3s and C-46s,
along with turboprops. After that, then it may be time to send her
out living full-time as a pilot to build up her flight time.”
“What about tradecraft?”
“We’ll start weapons training next week, along with escape and
evasion, surveillance and counter-surveillance techniques, and the
usual stuff,” Doris said.
“What about her femininity?”
“I think it’s time to see if she wants to start hormones,”
Janet replied. If she agrees and sticks with it for the next few
months, then it may be advisable to consider some non-genital
reassignment surgery.”

Sherry started working with Craig on her multi-engine rating
in the Twin Beech the next day, including a session on the care and
feeding of radial engines. “You can’t overprime a radial,” Craig
admonished. She learned about engines that measured their oil
levels in gallons, not quarts.
While Sherry was being introduced to the fun of engine-out
drills, a conference was underway concerning her progress. Col
Hampton had flown in, he met with Janet, Doris, and Dr. Trotti.
“How’s our boy doing,” was his first question.
Janet smiled. “She’s a woman, Colonel, and she’s doing fine.”
“Explain.”
“Frankly, I don’t think Sherry’s a transvestite. I think
she’s a transsexual, although she really hasn’t admitted it to
herself. The majority of TVs we get here aren’t content to go
full-time dressed up. They find some way of visibly asserting
their masculinity. The TSs assimilate completely. Sherry has
shown no signs of not wanting to be a woman. No covert strength
exercises, or anything like that.
“Her adjustment to female living has been remarkable, although
I don’t think she should consider making a living as a chef.” That
comment earned a laugh from Doris.

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.

The town (she thought of it as that) has several running courses
laid out along the roads, complete with mileage markers. Sherry’s
goal was to run three laps around the airport, a distance of over
seven miles.
The coursework was changing constantly. After a series of
lessons on clothing and accessories, Sherry started a basic cooking
course. Doris pointed out that most women knew how to do more than
fry hamburgers and eggs, which about the extent of Sherry’s kitchen
skills.

So she learned how to cook and how to select items from
the supermarket. Sherry privately didn’t think much of this phase
of her training. It seemed like a lot of effort to spend so much
time spreparing a meal that normally didn’t take anywhere near as
long to eat. Lord Sandwich knew what he was doing, she concluded

For most of the non-flying days, Doris had her wear more lady-
like attire. She got used to moving around in dresses, skirts, and
high heels. She lost her purse a few times the first week, but
soon carrying one became automatic.
The therapy was easier than she thought it would be. Sherry
trusted Janet and opened up to her completely. They met three
times a week, then scaled back to twice a week. Janet wanted to
make sure that the training wasn’t taking Sherry down a road she
didn’t want to go. But what she saw was a young woman who was full
of life. Sherry was finally doing everything she had wanted to do.

The deportment classes (to use Doris’s term) were more like
aerobics. The instructor’s name was Sharon, she worked to teach
Sherry to loosen up and move more fluidly, not to shamble along
like a male. They were tiring at first, but also fun. Sherry was
keeping up her running, she was now doing over four miles a day.