Learning Curves (December 2000-May 2001)
December 2000, and most of 2001 was the year of learning curves. Not curve singular-I had to
learn about having curves…in all the right places. It was a year of amazing growth, and not just
my chest, either. I can really say that this was the period of time where I learned just how feminine
I already was…how much I had become…and, how much I still had to go.
One of the two greatest problems that TG's face is getting read. The other is being caught with
feminine clothing, especially when your Significant Other is not aware of your being feminine….
December 4, 2000:
Dear Diary:
I'm getting sloppy! Saturday, after a trip to the shop (with minor luck), I had a pink shirt that I was
adding to the casual wardrobe and time got away…suddenly the S.O. is there! I recovered by holding
it up to her and checking the fit-it didn't. So back it went for a different one (that fits me very well!)
I'm also getting more daring-while the S.O. was trying on some maternity stuff, I bought a Joe Boxer
bra from Elder-Beerman! It's cute; I think Dan will like it, too. I need to go back and check for
matching panties…I also discovered that waist-cinchers are still made-I need one of these…especially
if I don't start exercising again soon!
I am so looking forward to my week of feminine fun-I really can't seem to wait-but I know I have to!
Luv `n hugs always,
Jayne
There was another time when I got to play. Here is the tale of how that went…
December 6, 2000:
Dear Diary:
Free at last! After taking the S.O. to the airport and seeing her off, I did my nails, came home in
panties and relaxed-missed church in the process. Did my toenails in Rose Aura, and just enjoyed
being a woman! Took all my clothes out to air, went to the shop and had a cock, went to rehearsal,
came home and was up past midnight playing (which includes that matching pair of thong panties
I bought from Elder-Beerman!) I wish I didn't have Christmas stuff this week-would love to go out
and play!
Luv `n hugs always,
Jayne
December 7, 2000:
Dear Diary:
Men can be such losers! I left rehearsal early tonight to see Dan, and he had a late business meeting
after his choir! After all the trouble I went through getting dressed for him, too! My night wasn't a
total loss, though-I managed a good cock at the shop tonight-and did finally get a waist cincher.
(I have hips! I like them, too!)
Back to this men thing, though-what on earth possesses someone to way overbook themselves? I
mean, that's what a planner is for, after all-except that guys seem to not really care. Especially that
one! I think we need to talk…
Luv `n hugs always,
Jayne
December 8, 2000:
Dear Diary:
Today is my birthday. I spent it well…I got dressed in my blue polo, jeans, black flat bra and hi-cut
panties, the waist-cincher, rings, earrings…and went to Someplace Else! I met a guy how thought my
name was "James"-and was he stunned when I told him it was Jayne, that I was TG, and so forth. He
reached out and grabbed my left boob, thinking it was a pad, and discovered that my boobs really
ARE 36c's! I asked him if he always groped strangers…It was hard not to laugh. I went from there to
the shop, and took part in a threesome. It was different, I must admit. I really enjoyed being female
tonight…especially after seeing the drag show upstairs. Bad, bad makeup jobs, and I felt I was built
much better-and I didn't need a whole wad of padding, either.
Luv `n hugs always,
Jayne
December 9, 2000:
Dear Diary:
After last night, tonight was somewhat anticlimactic. I mean, after all that happened, plus the little
shopping spree I went on…I knew as tired as I was, that it just wouldn't be as good. And, I was right.
Even a more judicious use of perfume than I did last night got me nowhere…even at the shop. Part of
my tired comes from Christmas stuff, and part of it…well, the S.O. is in danger of a miscarriage. The
baby should be about 10+ weeks…and it seems to have stopped at 6 weeks. To top it off, she's started
spotting. I should have stayed home and slept-but wanted noise. I struck out all over…still, when all is
said and done, I have enjoyed this time greatly-and now have to start the change back,. `cause I can't
do it all in one day. (sigh…)
Luv `n hugs always,
Jayne
There are times when I can share with others…at this point, I needed to open up some. Fortunately, I
had that ability, as my oldest sister just happens to be "family"-an active lesbian who has supported me
as she can…
December 18, 2000:
Dear Diary:
The S.O. lost the baby the 11th. I haven't had much time to process this. It is sad in a way, but it is also a
bit of a relief. All my secrets are safe for now…I got to speak to the Sis some last night; we talked for an
hour or so. She's got a letter coming my way soon-that should be interesting reading. I am also looking
forward (somewhat) to the vacation up and coming-I can use the time away from the midwest mindset
to rethink where am I at, and who I am as a person-and especially as a woman. Plus, I'll get a chance
to rest!
Luv `n hugs always,
Jayne
Yes, this was a tough time. But you know, I think it helped me in the long run. It made me really
understand that I was not the man I thought I was…but the woman I was becoming at that time. I
also missed being on the coast….
December 28, 2000:
Dear Diary:
…I miss being on the coast. I miss being "home"-where I can open up and be free. I dislike being
"straight" all day-and would love to get femme quick. However, I know that isn't practical right now,
so I will just have to wait for a better time. Hopefully, it'll be very soon. If not, well, I can wait.
Luv `n hugs always,
Jayne
Have you ever been glad to see a year end? Me, too.
December 31, 2000:
Dear Diary:
This will be the last entry for this year-and what a year it's been! J
I'm getting more comfortable as a woman, and more daring even yet: yesterday I got the S.O.'s mom to
buy me a set of women's sweats! They match the color of the warmup fleece I bought a while back…I
want to review all I've learned about me as a woman this year, so I can be a better woman next year.
There's always room for improvement!
Luv `n hugs always,
Jayne
About this time, I determined that being a woman suited me just fine. To that end, I switched from
New Phase to Estroven. I also bought a women's razor to start shaving my chest...just a little. A new
part of being this way also includes having a stable, long-term TG relationaship…well, I'm still
looking for that. One out of two isn't all that bad...!
January 10, 2001:
Dear Diary:
I hit the shop the other night…and got me a live one. All over each other, tongues in and out of
mouths, sucking cock…just what I needed! But…what I really need is a stable, long term TG relationship
-with someone who can be soft and warm and gentle. Someone who wants more than a quick suck or
fuck and then gone. Someone to share secrets with. Someone that would embrace my female side,
without being obnoxious about it.
I also need to write my own TG fiction-it seems like there ought to be a market for less sexual
fiction…Sometimes, I wonder if there really are others like me out there-but for now, I'll have to stick
with what's available through the `net.
Luv `n hugs always,
Jayne
I was forced into a rather indecent anal act at the end of the month. This next entry heralds my
'triumphant' return…
February 3, 2001:
Dear Diary:
Ooohhhh, Baby!
After buying sneakers, slacks, belts and barrettes yesterday-as well as gold-tone earrings-I did it.
Bathed, showered, shaved face and chest, dressed up really nice in the long sleeve black top, the new
stuff, hi-thigh panties and a pad, black t-shirt bra, gold necklace, black watch, ring, perfume and
mascara-and went out totally femme! Lip gloss, the works-went to the bank, the post office…and then
the shop. Jeff was there-and oh, my…even in the tummy cincher I was wearing (Hey…I said I went all
out…that means hips! J ), we still spent a most pleasant 30 minutes or so. Plus, I found $2.25 in tokens!
So-I'm okay; I have overcome the last trip down to the shop, and I feel so much better for the doing
of it. I just wish I could go on being a woman. I wore a bra and panties all last week; I will do so again
this week. I really like it!
Luv `n hugs always,
Jayne
It is interesting to see how my S.O. relates to all this. She got a turtleneck that, frankly, I was envious of.
The solution: we went shopping-together-to find one just like it…
February 20, 2001:
Dear Diary:
…Friday night we (the S.O. and I) went looking for a slate blue turtleneck. I liked the color, but it
seemed we were way too late: the Spring arrivals are out, in all their pastel glory. Wal-mart, Kmart,
Target…all the same story. Saturday was a near repeat: Marshall's, Penney's, Sears….
Sunday we went outlet mall hopping…and finally hit the jackpot at the Dress Barn Woman at the larger
outlet mall….
Luv `n hugs always,
Jayne
It was about here that I started shaving a part of my chest. And using a depilation cream, just
about down to where some of my bras hit. Good thing, too...Because there comes a time when
we have to make a decision: am I really serious about this womanhood thing, or am I just
playing games? That time for me finally arrived. Understand one thing: It is one thing to go
out in casual clothing and a little makeup. It is another thing totally to finally do the skirt
and pump thing for real…in public, where others can see you.
March 17, 2001:
Dear Diary:
What a rush!
I didn't stay out long-I was tired, after all-but to feel a cool breeze through my hose and under my
skirt was delicious! J I went out tonight, for the first time in a skirt…the black dance outfit. Black
sparkle blouse, medium length black skirt, black everything including pumps.
It was sorta quiet, and since I was very overdressed, I came home to change. Once home, though, I
decided against going back. I may not go out tonight, either-it's kind of nice to have the alone time.
Even so, I want to do this again and soon. What I really need is a casual skirt to dance in.
However, last night was an important step in my growth as a woman-and one I'm not gonna ever forget!
Luv `n hugs always,
Jayne
I started wearing hose at work shortly after this; in addition to a bra , panties, and a pad.
Things went quite well for a while. I even had a guy ask me once if I was in a drag revue!
This is where a new part of my life starts: Some people have met me only as Jayne Sakura…
and will only acknowledge me as such. Others know me as both male and female, and greet
me by masculine or feminine name, depending on how I am dressed, and if the S.O. is with me
or not. A good time of life, indeed.