I certainly started borrowing clothing from my mother’s drawers early in elementary school. I even sewed my own out of rags in junior high.

One thing really helped me determine and accept that I’m trans and that was to create a list of things I did and fantasized about throughout my life. I broke it down into major age groups such as:

- pre school

- elementary school

- junior high and high school 

- 20s

- 30s

- etc 

Within each timeframe I had a bulleted list of single sentences that reminded me of the event or activity. It took me some days to get it filled in because I kept remembering things that needed to be added. 

When it was complete I shared it with my therapist who remarked that he could not imagine someone who is not trans as having such a list, showing how my fantasies and feelings are such a consistent thread in my life.

This idea might help others too. But I recommend that you enter it into a file or write it out. Trying to keep it all in one’s mind is next to impossible and prevents one’s ability to see the whole picture. 

Dear Emma,

If it isn't too private, would you mind sharing it with us?

Think it would be a great example to the rest of us on making up our own.

Yours truly,

Monica

Well, you asked!

<6 years: preschool and kindergarten
Where I discovered my shame about wanting to be girly and do girly things, and the powerful need to keep it strictly hidden from others. But as an only child where did that shame come from? I assume I learned it from my mother, before I have memories, when I rebelled against her making me be a boy.

• Wore out my baby blanket’s satin edging; I loved the feel of it.
• Twirling like a ballerina at another child’s birthday party; ashamed and stopped before “being caught.”
• Wanted to learn to curtsey with the girls in preschool
• Playing with the girls in the kindergarten kitchenettes; afraid of the boys play and what they would think
• Playing with neighbor friend (who much later came out as gay): making up stories with little characters

6-12 years: grade school
Like a sponge I soaked up knowledge about girls and women, contemplated what it would be like, and fostered fantasies. I spent hours surreptitiously investigating in magazines, newspapers, television, and catalogs.

• Wanted to be a Blue Bird in 1st grade
• Wished I could be a mermaid
• Wanted stirrup pants like the girls: how would they feel to wear?
• Rolled up in my Nana’s satin comforter; shamed by her to stop.
• Playground: with the girls playing hopscotch, gymnastics on bars
•  Unexpressed wishing mother would buy leotard and tights for me
• Bedtime fantasies of being dressed as a girl, transported away into space. Or, dressed in a harem girl’s costume, living in an I Dream of Jeanie bottle, with Jeanie.
• Fixated on catalog with sleeping bra, wanting one, trying to figure out how to order and receive it secretly.
• TV: That Girl, Girl from UNCLE, Flying Nun, The Avengers, I Dream of Jeanie, Bewitched
• Favorite movies: Patty Duke, The Sound of Music, Three Lives of Thomasina
• Wanted to be able to cry and wear a ring like a girl at school

13-18 years: junior and high school
Covert actions taken to experience clothing, the good feelings that emerged were undeniable.

• Subtly" trying to encourage mother to buy a tutu for me
• Hand-sewing camisole and romper out of rags while parents at AA meetings
• Trying on girdles from Goodwill bag
• Cutting panties from discarded pantyhose to wear under clothing or to bed
• Bought black long-sleeved leotard at dance clothing store; returned a year later to buy black tights. I had to wait or risk their remembering me.
• Wearing mother’s swimming suit when parents were out for the evening
• Lake Berryessa: bought pantyhose to wear and hang out in, on weekend alone. It felt marvelous but lonely.
• Wanted to crossdress with girlfriend; she was okay with it but I was too cautious
• Stole girl's skirt, top, and slip from restaurant restroom
• Continually looking for discarded/lost girl’s clothing
• Found yellow girly panties on lawn
• Found multicolored panties in HS parking lot

18-24 years: college
More clothing and my first-time experience going out dressed. But otherwise a low point in my TG world as I tried to be what I was supposed to be.

• Stole blue leotard from clothes wash room in dorm
• Halloween: dressed as coed (skirt, girls sweater) for party, loving it and yet feeling so alone, afraid to show that I loved it too much and that I’d be found out. Twenties
• More clothing and dressing.
• Found navy blue dance panties in parking lot
• Bought leotard and tights at dance store
• Bought leotard at flea market
• Halloween (1981): on the Castro as a nurse. What a great time I had, just being me if only for a few hours.
• Halloween (1982): on the Castro as a bride. Not quite as much fun but a good time nonetheless.
• Wearing leotard/panties during sex

Thirties

Explorations, confronting fears by buying clothing.

• Wearing panties and nightgown during sex
• Visited TV/TS bar in Munich: a long walk from my hotel but I left shortly after arrival; too scared.
• Foxy Lady Boutique – SF: dress and lingerie
• Lingerie boutique - Mountain View: corset and stockings

Forties
Exploring what it means, terrified to come out and be accepted. Once again, full withdrawal.

• Accumulating very small wardrobe
• KOA Santa Cruz: much research, writing, desperate for acceptance and understanding. Drove to LA to crossdressing clothing store; bought a dress, lingerie.
• Delivered overly comprehensive report to my wife that I hoped she would see it all as no big deal. Just the opposite, she was devastated.
• Serious suicide considerations
• Carla's Boutique: bought dress, bra, other

Fifties
Discovering the new transgender vocabulary, that being trans is inborn, not a choice. Wondering how far on the spectrum I will need to travel. Finally: full disclosure with therapist, wife, and gender therapist.

• Bringing leotard and tights on business trips
• It all emerges again: much more exploration
• Confrontations with wife
• Serious suicide attempts, much consideration
• Clothing bought on Amazon, REI, Carla’s, dance store...
• Judy Van Maasdam’s confirmation
• Attended TG/TS group meetings at Carla's and with Judy
• Participation in on-line support groups TGGuide and CrossdreamLife
• Wearing dresses and skirts in private at home; nightgown to bed

Sixties
With disclosures, my shame is about gone. Still hard to accept this reality at times. What will I do if my marriage collapses and I’m on my own?

• Realization that I'd always wanted to be small and treasured: does that mean female, or perhaps loved by my mother? I think it's the former but it's probably both.
• Wearing dresses and skirts in private at home; nightgown to bed
• Coming out to family and friends: all going relatively well
• Increasingly accepting that I do not see a need to socially or surgically transition
• Attended TDoV, TDoR in San Francisco; surprised I don’t feel much of a bond with these people.
• Dara Hoffman-Fox’s book (You and Your Gender Identity: A Guide to Discovery) and workbook: worked through the exercises, provided them with edits for their 2nd edition.
• Three days of transformation, living, and going out at Over The Rainbow in Portland. I loved it.
• Building up cosmetics, having fun experimenting and learning.

Update (Summer 2017 thru September 2018)
Started transitioning to Emma just over a year ago, living full time, never happier or more at peace in my life. No thoughts or worries about “de-transitioning.” Still some social anxiety but mostly gone. Life’s good.

• 100% out to all professional colleagues, friends, family. Most are very supportive, I even learned from one colleague that his son is possibly trans or gender variant.
• Divorce finalized December 2017; she and I still talk at least weekly, often for an hour or more, listening to each other, support, shoulder to cry on.
• Gender Odyssey Conference (Seattle): Attended August 2017, dressed as a woman (wig and all) for three days. Wonderful experience, learned a lot, made new friends. August 2018: attended all four days as a Session Host, had a fantastic time introducing speakers, managing the room, helping and talking with attendees.
• Started HRT 9/11/17: Consulted with an endocrinologist with an idea for an experiment for low-dose HRT. He agreed, I tried it, and loved it. Never looked back.
• Donated all of my male clothing to charity, now very comfortable shopping anywhere.
• Feminine voice training with Sandy Hirsch: went very well
• Legally changed my name and gender marker in all state and federai records
• Happily accepted by local lesbian groups for hiking, camping, and just fun. Several new and great friends.
• Joined Human Rights Campaign as a volunteer; hoping for greater responsibilities soon.
• GCS scheduled for 1/31/19.
   

Yes, :"We've all known each other all our lives, just never met each other."  So many similarities go on and on.

Thank you Emma, that I s so close to me through college.  Obviously some of the details are a little different, but it looks very familiar.

"These few hours with this crowd has been the some of most enjoyable time I have spent in recent memory, even though it was just hanging out and watching anime."

Well done Tilly - That was a brave step, I am so glad that you enjoyed your time out with your friends! 💛

Dear Christy,

Would love to see your list, if you are comfortable.

Feel all you ladies are helping many more than you will ever know!  💄👑👒👗👙👠👡👢👚👜👝👛

Gratefully yours,

Monica

For the bravery issue, I have lucked into the most understanding group of friends I could ever ask for.  My biggest regret is that my friends have probably seen more of the real me then my wife.  Out of respect for her (and the sanity of our daughter) I have limited my change in clothing around her to undergarments. 

I am still looking for a therapist though...regardless of how wonderful my friends are (both here and in real life,) I still believe a professional would help get through this with less agony.

Tilly