Watershed moment?

Hi Girls,

Was there a "watershed" moment in your dressing career? I can't decide between two. It was either getting my ears pierced or shaving my legs for the first time. Both were game-changers

I could recall many but yours sure are at the top of the list. I believe a huge one was when I had told my wife and she came home one day with a pink bra and panties set. The most watershed moments came after joining here and reading about things I never thought of. I never thought about make-up and jewelry and breast forms and when I started to see a much complete Maria I was always very emotional when looking in the mirror. A few that stick out more then others was the day I decided to go to a crossdressing store to buy a pair of heels. That day I took off my male shoes and exposing my pantyhose feet to a stranger and walked around the store wearing heels with other customers coming in. The other was when I shaved my body and couldn't believe how everything felt so different, so much better, it felt like a huge achievement. I wrote about it lately that my sister in law gave my wife a bag of clothes to give to me and I was so emotional. My wife didn't understand it, but it was a feeling of acceptance. Just sitting here writing this as I'm wearing a pink long silk nighty with my wife next to me can bring on some watershed.

Telling my wife of my proclivity and gaining her acceptance rather than rejection. My femme persona flourished after that.

I also would say the first time shaving my legs.

Discovering new york city, going out and finding acceptance.

Like Kris, telling and being accepted by my wife. She?s been supportive and very helpful. A blessing.

Some years back, tired of the binge/purge cycle and its attendant stress, I decided I would dress every day for at least 15 minutes, whether I felt like it our not.

That was a game changer for me.

Well initially it would be my very first experience which I?m pretty sure was putting on a OBG found in the bathroom hamper when I?m guessing I was about 5. That sensuous and secure feeling just felt perfect.
Another was 50 years later when purchasing my first set of breast forms, after all those years of simulating boobs from various materials.

Telling my doctor about my “situation” and receiving my first hormone related prescriptions. The doctor was very kind and understanding.

Wearing a wig for the first time enabled me to see that I would look female enough to go out in public.

When my wife dared me to shock her. So she came out of the shower to find me in the top and skirt that she knew I had, but also a bra, stockings, and garter belt. That led to "the talk", which went well. And the floodgates opened. :)

The first was when I was a young child finding my mother’s girdle and hose in her dresser drawer and slipping the on. The latest was sixty five years later when I allowed my wife to find me in her panties and having her offer to buy some of my own for me.

I had never dressed beyond lingerie for the first 50 plus years of my life. I always assumed I would look ludicrous. My wife was working away several nights each week. That time alone led me to experiment more than in the past. I am not sure how it happened. Perhaps out of boredom or curiosity, i borrowed one of her tops and a skirt. A few night later I tried makeup for the first time. I vividly recall the moment: fully dressed and made up (at least to the extent of my ability at the time). I caught a glimpse of myself in the mirror and instead of being embarrassed or repelled, I thought, ?I can do this!?

It was a redefining moment. I gave myself permission to do something I had hardly dared admit to myself. Within a few weeks I had gone out dressed, been fitted for a wig, gotten a makeover and began spending much more of my day to day life en femme.

I had been shaving my legs for some time already. But when I finally had had enough, I shaved the rest of my body down. That was the point at which I knew that my possibilities had just opened up.

Shaving my entire body for the first time was a huge transformational moment but the biggest one was definitely prior to that when I saw my face with full makeup without the full mustache I had for many years.

When I got make-up right-ish for the first time and then I put a wig on in front of a mirror and at that moment everything I did just clicked together and instead of ridiculously looking guy there was a cutie looking back at me.

Buying a breastplate. After that, I put a lot more effort in to look good. (in my mind)
Better wigs, make up practice, spending longer dressed.

I mentioned this in another post just a few minutes ago...

Back in my early/mid 20s, I purged and stopped crossdressing for 2.5 years due to a young lady I was dating at the time. When I finally put on pantyhose for the first time after that drought...the psychological explosion inside my head was intense. I'm not talking about physical reactions, but my mental reaction. It was the first moment that I finally realized that crossdressing was permanently part of me. It finally...finally...set me on the road towards self acceptance.

More recently; like April Rose I've been crossdressing every day now every day this year. Mostly, it's while sleeping (pantyhose or stockings, bra and forms, nightgown). But, it's every day. Today I was crossdressed from about 8 a.m. until a bit past noon (working from home). I've been doing this for a variety of reasons, but one of them is to see where this mentally puts me with crossdressing after so much of it. At times, I haven't felt too keen about crossdressing but by the time I get crossdressed I'm glad I did. I'm still processing what this says to me. My wife is wondering if I'll dress full time once we retire. I don't think so, but I do think I could comfortably be 100% at home if I wanted to. It's an interesting experiment anyway, and is flipping the script on crossdressing a bit, with it being the norm rather than the more uncommon.

The big one was discovering this site. I started reading the posts and thought "that is so me!" For a while, I would wake up crying tears of joy, because I had found my true self.

- dressing for therapy session for the first time (this is where i first 'owned it' for myself)
- my wife picking out a cute mint green mini-sundress at a Marshall's store and asking if I'd like it. I'd never mentioned wanting a dress to her before this. She laughed at me when i modeled it for her so it dropped a notch on this list
- Pierced ears
- first manscaping leading to perpetual full body shave
- wearing eye makeup out of the house for the first time in drab mode (regular occurrence now)

Definitely shaving all my body hair off, especially my legs and chest.

The first time I saw myself fully transformed.

I had gone to a transformation service in Piscataway, New Jersey. Lady Ellen did my make up, hair and picked out an outfit for me including bra and breast forms. I was prohibited from looking at myself in a mirror until I was completely transformed. The first time I saw myself as Ingrid, in the mirror, the feeling that went through my body was something I had never felt before in my life and I never want it to go away.

Perhaps my watershed moment was actually a combination of events. I finally got up the courage to contact a local CD group and went out dressed to my first meeting, which was held in a private clubhouse location. That was momentous, but what happened a few months later was even more significant. The group was holding a holiday party at a restaurant in a nearby mall . That was the first time out in the general public. I've since been out many times once I realized that I could "pass" or at least would be good enough to pass.

I don't remember any watershed moment that changed my life for ever. However, I am sure that I was lost when having tried high heels and a garter belt for the first time.

Telling my then girlfriend now wife that I was a crossdresser. I just knew I could no longer hide it.