If you're new to my story, I realize that 63 chapters is a LOT to catch up! This chapter is a brief summary of my story to bring you completely up to date with the back story and so you can read forward without missing anything. (Of course, you're welcomed to read from Chapter 1 forward, but this is my diary, and it's LONG.)
I'm Christy. At this point in my diary, I'm 15 and I'm a fresh-person at a small, upscale private school (you know, uniforms and Moms driving BMWs) in the suburbs of a major American city. I live at home with my widowed Mom who runs a home-based wealth management biz. My dad died unexpectedly a few years ago. At the beginning of the story, my sister Rebecca (who occasionally goes by Becca or Becky as the mood strikes her).
The cast of characters:
My Mom, who has proven VERY supportive of her new daughter
Becca, my sister, who loans me her used clothes
Our dog, Princess
Aunt Lilly, her divorced best friend who owns an upscale women's clothing boutique and has a teenage son my age named Jason.
My co-hort of best friends who call themselves the sister wives': Brianna (who is my absolute bestie and calls herself Brie' right now), Maddie (who's dumb as a rock and comes from a `semi' strict religious family), Emma-red (who is on student council), and Emma-brunette (who dates Eric the jock). Later Randi joins the sister-wives as a newbie to our school and a love-interest for Brie.
Carlos, my boyfriend, an 11th grader who is kinda `bi' but mainly only as a top.
Ms. Weston, the headmistress of the school, who is accepting when I `come out' and only wants to make sure I don't get bullied and fit in well.
Mr. Petrie, the long-suffering guidance counselor, is tasked by Ms. Weston with making sure I fit in.
Mr. McCarthy, the drama teacher and drama club coach
Dr. Preston, my endocrinologist/therapist, who I refer to as `Doc Strange' cuz of the way he looks
Ms. Hargrove, my sex therapist, who I refer to as `Ms. Weasley' cuz of her absolutely messed up office
Martha, who runs a sex shop that caters to a lot of folks in the trans community but also strippers and people who just want to buy erotic-ware and such.
Keith, a professional photographer
Brandy, Keith's make-up artist and sometimes helper
There are some others who come and go, but that's the main cast of characters.
As a bit of a back story, everyone thinks I'm the most effeminate gay boy they've ever met, but I don't realize it. At school, I blend into the scenery and hang mainly with the sister wives who treat me like their pet, but again I'm just oblivious to stuff like gay' or straight' or whatever.
One night, right before school begins, Mom and Lilly go out for the evening. (I'm so clueless, I don't even realize it's a date'.) Mom doesn't know (or does she?) that I dress in her clothes when she's not here and feel a lot more comfortable like that. I attempt to put on her makeup, but I'm terrible at it. My hair is kinda long-ish and if I comb it right, it looks fairly girlish. I'm always careful to put her stuff away and clean up before she gets home, but on this night, I screw up and fall asleep on the couch watching a movie. Mom comes home early and discovers me in one of her sexiest night gowns (which doesn't at all fit me) and I break down in tears. At this point, I don't think of myself as trans' or a `crossdresser' or anything like that, I just know I'm more comfie in feminine clothes.
Rather than be mad, Mom hugs me and tells me that she's long suspected I was wearing her clothes, and if that's what makes me more comfortable, then she's OK with it. She helps me take off the makeup properly and finds me a more comfortable but girlish set of jammies to wear to bed.
Soon, Mom hooks me up with Dr. Preston, who quickly diagnoses my gender issues and prescribes gender affirming care, which will include living full-time as a girl. Ms. Weston helps me transition at school, and Mr. Petrie arranges for me to join the drama club to find an outlet of (hopefully) accepting artists. The sister-wives are all enthused, because now I've given them a project! Brie is particularly helpful, since she and I are very close in size (and both have Jennifer Lawrence posters on our bedroom walls -- me because I want to be her, and Brie because she wants to sleep with her!). I switch over to wearing girl' school uniforms rather than boy', and no one at school seems to notice the difference (or at least they all seem to act like, `well, yeah, we could have predicted THAT!'). It's a VERY liberal school, and I'm lucky to be there.
We have a school formal in the Fall, and Brie finds me just the right dress to wear. Eric introduces me to Carlos, who is also in the drama club, and he and I hit it off. We dance together, and later at the end of the party, he walks me to the parking lot. We stop and kiss on the way. Later, Carlos and I start dating, and we find ways and places to become sexually active.
In the late winter, Martha convinces me to model for her. She says I'm coming along fantastically in my transition, and she wants to feature me in a picture book she has to provide guidance for other young girls trying out new fashions in their transitions. I reluctantly agree, and this leads to other modeling assignments via Keith her photographer. Eventually, Becca gets into the mix as well, and we do a modeling shoot for Lilly's boutique.
COVID hits our area like a ton of bricks. We all end up becoming hermits. Becca moves back from college and Lilly's boutique becomes on-line only (hence, Becca and I becoming her models). The spring becomes really boring. Doc Strange changes my hormone mix a bit, and my boobie and butt start fleshing out, but it's not like anyone's gonna see `em!
Finally, in late May, after w-a-a-a-a-y too long as hermits, Carlos and I both test negative for COVID and get away for a Saturday rendezvous. Martha wants me to model some swimwear, and I arrange for Carlos to be the audience of one. Later, he and I have a furtive consummation in his car.
You're welcome to read the whole story, but it's a very long book up to this point! I'll keep editing my old diary pages and posting them here for you to enjoy. Please let me know if you're enjoying this, and please contribute to Nifty to support this at https://donate.nifty.org/.